Handover of Hong Kong The Death of Diana, Princess of Wales · The transfer was arranged to...
7
JACS Year Review 1997 Baran Lab Group Meeting Cheng Bi 10/20/18 Handover of Hong Kong On 1 July 1997, the British government officially transferred the sovereignty of Hong Kong to People’s Republic of China. The transfer was arranged to coincide with the expiration of this lease on the previous day, 30 June 1997. This event marked the end of British rule in Hong Kong, and is regarded by some as the end of the British Empire The Death of Diana, Princess of Wales On 31 August 1997, Diana was killed in a car crash in Paris. In her funeral, Diana's brother Lord Spencer, and representatives of some of her charities. Lord Spencer said of his sister, "She proved in the last year that she needed no royal title to continue to generate her particular brand of magic." Viable offspring derived from fetal and adult mammalian cells Nature. 1997, 385, 27 In July 4, 1997, Mars pathfinder landed in Mars In 26 June 1997, the Philosopher's Stone by J. K. Rowling got published Top five moives by IMBD in 1997
Transcript of Handover of Hong Kong The Death of Diana, Princess of Wales · The transfer was arranged to...
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
Handover of Hong KongOn 1 July 1997, the British government officially transferred the sovereignty of Hong Kong to People’s Republic of China. The transfer was arranged to coincide with the expiration of this lease on the previous day, 30 June 1997. This event marked the end of British rule in Hong Kong, and is regarded by some as the end of the British Empire
The Death of Diana, Princess of WalesOn 31 August 1997, Diana was killed in a car crash in Paris.
In her funeral, Diana's brother Lord Spencer, and representatives of some of her charities. Lord Spencer said of his sister, "She proved in the last year that she needed no royal title to continue to generate her particular brand of magic."
Viable offspring derived from fetal and adult mammalian cellsNature. 1997, 385, 27
In July 4, 1997, Mars pathfinder landed in Mars
In 26 June 1997, the Philosopher's Stone by J. K. Rowling got published
Top five moives by IMBD in 1997
X
H3C H
H OOEt
HEtO
X = ENG
Mohrig, J. R. et al., JACS, 1997, 479
H3C
F
HCO2H
H
H
NC
Rosenberg, R. E. et al., JACS, 1997, 487
C Si
inversionretension
10 kcal/mol lower
VS.
Yamabe, T. et al., JACS, 1997, 807
N
NMe2
tBu
OMeO O
Me
Cl3CMe
N
NMe2
tBu
OBnO O
Me
MeMe+
OH
1-naph
H3CH
MgBr2, Et3N O O
Me
Cl3CMe
O 1-naph
CH3H
O OMe
MeMeO 1-naph
H3C H
+
yield 46%, ee 88% yield 49%, ee 95%
Parallel Kinetic Resolution
[no mutual interference][similar rates][complementary enantioselectivity][distinct product]
Vedejs, E. et al., JACS, 1997, 2584
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
SS
LiS
S
Li
SS
Ph
Li SLi S
Ph[X-Ray]
SS
Ph
Li
σ* ✓
n* ✗
Juaristi, E. et al., JACS, 1997, 7545
OCO2Me
Ar SnBu3
BF3OEt2
M Ar SnBu3
M
Ar SnBu3
MAr
M = SnBu3, 84%, A:B = 100:0; M = SiMe3, 85%, A:B = 7:93A B
+
Snγ-effect of SnYoshida, J. et al., JACS, 1997, 11986
O
OtBu
NHEt OH
Me SePhMe
Me2SiCl2, i-Pr2NEtEt3B, BuSnH Et3B, BuSnH
MgBr2OEt2, i-Pr2NEt
[exo-cyclic effect]
O
OtBu
NH O
MeMe
Et [Si]O
OtBu
NH O
MeMe
Et
HN
[Si]O
MeEtO
OtBuHBu3Sn H
[Mg]O
OOtBu
MeHN
Et Me
Bu3Sn H
O
OtBu
NHEt OH
Me Me
O
OtBu
NHEt OH
Me Me
(anti product) (syn product)
Guindon, Y. et al., JACS, 1997, 9289
CH3
D
Ph
Ph MeOH, DCB
hv (300 nm) Ph
Ph
DCH3
OCH3
[complete inversion]
CH3
D
Ph
Ph
[3 e- SN2]
Dinnocenzo, J. P. et al., JACS, 1997, 987 and 994O
O
OO
O
HOH
HO
1. 1,4-Dicyanodurenehv (300 nm)
yield 21%, ee > 99%Demuth, M. et al., JACS, 1997, 1129
[Mg]
[exo-cyclic] [endo-cyclic]
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
N
R2
R1
NMe2
t-BuLi, ZnBr2N
R2
R1
NMe2MgBr
N
R2
R1
NMe2
MgBr
ZnBr
ZnBr1, E1+
2, E2+
N
R2
R1
NMe2
E1
E2
Nakamura, E. et al., JACS, 1997, 5457
OSiCl3
RCHOLewis acid
RCHO(S, S)-4
O OH
R
O OH
ROSiO
R
HOP(NR’2)3
ClCl
OSi
O
H
R
Cl ClCl
NH
P
HN O
N
Ph
Ph
(S, S)-4
Denmark, S. E. et al., JACS, 1997, 2333
EWG
EWG
EWG
EWGtBu
tBuHgCl/DABCOhv
EWG = CN CHO CO2EtYield = 99% 46% 84%
Russell, G. A. et al., JACS, 1997, 8795
N
N(OC)4W
O
Me
Me
Me
+ 1. DCM, 60 oC
ON
NO
H3C
CH3
Me
ON
NO
H3C
CH3
Me
(exo) 84 (endo) 16:
+2. CAN, 65%
Wulff, W. D. et al., JACS, 1997, 6438
Liu, R. S. et al., JACS, 1997, 4404
R1HO OW
R1
Ph BF3OH
[dication synthon]
OR1
Ph
R2
R21. W-Cl, CuIEt2NH
W = CpW(CO)3
2. PhCHOR2MgBr
O
R1 H
N
R1 H
R2
+OSiMe3
R3 R4+0.2 eq Yb(OTf)3
- 45 oC
O
R3
R4
HN
R1
O
R3
R4
OH
R1
R2
> 83 % trace1 eq 1 eq 1 eqKobayashi, S. et al., JACS, 1997, 10049
Nicholas, K. M. et al., JACS, 1997, 3302
NHPh
FeCl2/FeCl3 (10 mol%)70-100 oC, dioxane
PhNHOH+
[sole product]
ON
Ph
FeCl2FeCl3 PhNHOH
PhNO++
OFeO
O OO O
PhN
PhN
NPhNPh
NPh
PhN
2+
2FeCl4-
tBuO tBuO
SO2Ph
1. Ni(COD)2(13 mol%)2. Na/Hg
88%+
tBuOOH
tBuO
OH
H
OHtBuO
1. Hg(OTf)2
2. LiAlH480%
Jones’ reagent88%
1. m-CPBA88% HO
Lautens, M. et al., JACS, 1997, 623
2. LiAlH491%
O
X
C
H SiMe3
O
X
H
1. hv 2. Bu4NF
X = O,NBocee> 85%
Carreira, E. M. et al.,JACS, 1997, 2597
Cl
Me
OSiPh2
SnMe3
Me
2 eq. n-BuLiTHF, - 78oCr.t., Me3SiCl
68%
SiPh2OSiMe3
Me
Me
NSiPh2
SnMe3
SiMe32 eq. t-BuLiTHF, - 45oC
Me3SiCl, 86%SiPh2
NSiMe3
Me3Si
Tamao, K. et al., JACS, 1997, 233
O
O
O R2
R1
XOH
OH
O R2
R1
X
OCH3
350 nm
MeOH~40%
[No Heat] [No Base] [No Acid]
Smart, R. P. et al., JACS, 1997, 461
PtBu2
Ir
PtBu2
H
H+
150 oC, 1 h +
[solvent][the first catalytic system]
54 44:
Gupta, M. et al., JACS, 1997, 840
ClO8 eq SmI2
50 atm CO
THF, 50 oChv > 400 nm
Ogawa, A. et al., JACS, 1997, 274568%
N
MePh
Ph
N
Me
Ph
Ph
CH3CN110 oC
88%
N
Me
Ph
Ph
Kerwin, S. M. et al., JACS, 1997, 1464
N
O
O
HOH
CO2LiN
O
H
CO2Bn
CO2Me
R1. BnBr then O3
2. MeCN80-100 oC32 ~ 63%
CO2Me
R
+
Gallagher, T. et al., JACS, 1997, 2309
Ph Ph
PhPh
N
Ph
PhCOCH3
hv
Ph PhPh
PhN
Ph
N
Ph Ph
Ph
Ph
Ph
+
Armesto, D. et al., JACS, 1997, 12659
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
Me3Si
Me3Si
O
O
Me3Si CO
C SiMe3R1
R2
1. Ph3PCR1R2X
2. hv
[nice solid][bench stable]
[benzene synthon]?
Tidwell, T. T. et al., JACS, 1997, 2832
C
R1
R2
Me Me O
R1
R2Me
Me
[Rh(cod)2]PF6-(R, R)-Me-DuPhos
5 atm COyield > 87%, ee > 65%Murakami, M. et al., JACS, 1997, 2950
NCH3
1. [C], 77 K
2. MeOD
[C], MeOD
77 KNCH3
D NCH3
D
[thermodynamic] [kinetic]
NCH3
3-dehydropyridiniumylid
NCH3
H H
HH NCH3
D D
DD+C, 77 K [crossover
product][intermolecular
mechanism]
N
E
N E
O2 E+
Shevlin, P. B. et al., JACS, 1997, 5091
R1
OHR2
R1
OH
OOH
R2
1. TPP, O2hv
2. DTBNtBuOOH
Dussault, P. H. et al.,JACS, 1997, 3824
R
Br
RCp2ZrBu2, PMe3
50 oC, > 81%
SiMe3Me3Si
Br+
Cp2ZrBu2
D2O
I2
Me3Si SiMe3
DMe3Si SiMe3
ITakahashi, T. et al., JACS, 1997, 4561
Ar TBDMS I
TBDMSAr
Ar
IPy2BF4/HBF4
DCM, -80~-30 oC95~98%
2
TBDMS
I
Cl
Ph
IPy2BF4/HBF4
IPh
I
Cl
76%
Barluenga, J. et al., JACS, 1997, 6933
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
O
Me Pd(OAc)2dppe
Me
Me OLi
OEt
Me
Me Me
O
OEtOH
1. TBDMSCl2. LAH
3. Swern
PO
EtOEtO
O
OEt4.
Me
Me MeOTBDMS
O
OEt1. DIBAL-H2. Swern
3. HOCH2CH2OH
Me
Me MeOH
O
O
1. TBAF2. DMSO, SO3-Py
Me
Me Me
O
O
H
O
1. propargylGrignard
2. TBDMSCl
3. APTS
OH
Me
Me
Me
OTBDMS
1. NIS2. CrCl2(THF)2
OTBDMS
HOO
Me
Me
Me
OTBDMS
SiBr
Me Me
1. AIBNBu3SnH
2. H2O2/HF
OH
Me
Me
Me
OTBDMS
H
H
OH OH
Me
Me
Me
OH
H
H
OH
TBAF
epi-IlludolMalacria, M. et al., JACS, 1997, 3427
VancomycinEvans, D. A. et al., JACS, 1997, 3417Evans, D. A. et al., JACS, 1997, 3419Nicolaou, K. C. et al., JACS, 1997, 3421
other total synthesis not coveredDanishefshy, S. J. et al., JACS, 1997, 6686Magnus, P. et al., JACS, 1997, 6739Guitian, E. et al., JACS, 1997, 3028
Myers, A. G. et al., JACS, 1997, 6072Bonjoch, J. et al., JACS, 1997, 7230Wender, P. A. et al., JACS, 1997, 7897
methodology papersinteresting but not covered
desymmetrizationHarada, T. et al., JACS, 1997, 9067
Fujioka, H. et al., JACS, 1997, 12016Trost, B. M. et al., JACS, 1997, 2735
amino acid synthesisCarreira, E. M. et al., JACS, 1997, 8379
Myers, A. G. et al., JACS, 1997, 656Petasis, N. A. et al., JACS, 1997, 445
alkyne derivatizationConnor, J. M. et al., JACS, 1997, 3631
Mori, M. et al., JACS, 1997, 12388
Trost, B. M. et al., JACS, 1997, 7595
Trost, B. M. et al., JACS, 1997, 698Yamamoto, Y. et al., JACS, 1997, 4547
bimetallic systemIkeda, S. et al., JACS, 1997, 4779
Montgomery, J. et al., JACS, 1997, 4911
Yamamoto, Y. et al., JACS, 1997, 6781
Montgomery, J. et al., JACS, 1997, 9065
cycloadditionWest, F. G. et al., JACS, 1997, 2066
asymmetric synthesis
Denmark, S. E. et al., JACS, 1997, 125Zhang, X. et al., JACS, 1997, 3836Paquette, L. A. et al., JACS, 1997,
1230, 1242 and 3038
Leahy, J. W. et al., JACS, 1997, 4317Rawal, V. H. et al., JACS, 1997, 7165
ClSi
BrMe Me
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
OOH 1. BnBr, NaH
2. KCN, MeOH3. TBSCl
OBn
OTBS
CN
1. disiamylboranethe H2O22. Swern
OHC
OBn
OTBS
CN
OBn
OTBS
CNHAcO
1. HCCMgBr2. Ac2O
1. (Me2PhSi)2CuCNLi22. DIBAL-H OBn
OTBSCHO
CH
SiPhMe2
H
O
O
Br
NPPh3
C
H
N
Ar
Ar =OBn
OTBSPhMe2Si
H
1. mesitylene, reflux2. TBAF
NHBr
H
H
O
O
OBn
OTBS1. Lindlar, H22. Pd(PPh3)
3. TsClN
H
HTs
O
O
OBn
OTBS
1. DMDO2. FeCl3
3. DIBAL-HN
H
HTs
O
O
OBn
OTBS
HO1. Pd/C, H2
2. Na/naphthalene
3. PPh3, I2N
H
H
O
O
OH
OTBS
1. TPAP, NMO2. LDA, TMSCl
3. Pd(OAc)2N H
O
O OTBS
O
1. TBAF2. (MeO)3CH
N H
O
O OH3. DIBAL-H
OMe
(-)-Coccinine
Weinreb, S. W. et al., JACS, 1997, 2050
CO2Et
Br
Me Me
Br
Me Me
SPh
Me Me
SPhCO2Me
O
H3CH3C
SPh
CO
SPh
H3C CH3
H3CH3C
SPh
OLi
H3CH3C
SPhOLi
H3CH3C
SPhO
CH3
H3CH3C
AcO CH3
H3CH3C
AcO CH3
O
H3CH3C
OCH3
(-)-Salsolene Oxide
O
Me
Me
Me
H
Me H
H
H
HO
Me
H
H
H
MeMe
MeMe
Me
H
Me HH
HOH
X(+)-Epoxydictymene Paquette, L. A. et al.Schreiber, S. L. et al.
1. DIBAL-H2. PhSH, TiCl4
1. NaI, heat2. LDA
CO2Me
1. KOH/H2O2. (COCl)2
C6H6, reflux CH2CHLi CH3I1. LiAlH4
2. Li, EtNH2
3. Ac2O, py
m-CPBA 1. LiAlH4
2. Martin’ssulfurane
Paquette, L. A. et al., JACS, 1997, 2767
JACS Year Review 1997Baran Lab Group MeetingCheng Bi10/20/18
O
Me
Me
HH
[racemic]
MeN SPh
O
Me n-BuLi
then 170 oC
O
Me
Me
HH
[enantiopure]
MeOHC
MeO2C
Me
1. LDA, TMSCl2. O3, Me2S
3. CH2N2
Br Me
Met-BuLi1.
2. KOH/MeOH O
O MeH
H
Me
Me
[major]
1. Tebbe’s reagent
2. i-Bu3Al Me
Me
OH
H
Me
Me
H
1. LDA, (PhS)2
2. DIBAL-HMe
Me
HOH
H
Me
Me
HPhS
1. DET, Ti(Oi-Pr)4,PhC(Me)2OOH
2. NBSMe
Me
H
H
Me
Me
HPhS
[major]
BrOO Me
Me
H
H
Me
Me
O
1. Bu3SnHAIBN
2. PhCl160 oC
1. B2H6/H2O22. PCC
3. LiN(SiMe)3Me
Me
H
H
Me
Me
OO
H[dead end]
Me
Me
H
H
Me
Me
H
Me
Me
H
H
Me
Me
H
O
OMe
MOMO
1. LAH2. COCl23. PhSeH
4. (TMS)3SiHAIBN Me
Me
H
H
Me
Me
H Me
MOMO Me
Me
H
H
Me
Me
H Me
Me
Me
H
H
Me
Me
Me
O
H
[end game]
steps+
1. HCl/MeOH
O
2. PCC
[major]
1. LDATMSCl2. DDQ
3. Li/NH34. PCC
MeMe
Me
O
Me
O
OH
H MeMe
1. Br22. NaOMe/MeOH
3. KOH4. H2SO4
Me OHH
H Me[major]
1. LiAlH42. Ac2O
3. NaOMe
Me OHH
HMe3Si
1. BuLi, TMSCl2. K2CO3/MeOH
2. n-BuLi, A-1
Me H
HMe3Si
O
OMe
Me
CH3CN, refluxor
ultrosoundor NMO
Me H
H
Co(CO)3Co(CO)3
OMe Me
OH
Me H
H
Co(CO)3Co(CO)3
OMe Me
OMe
Me
Me
H
H
H
H
O [dead end]
1. Co2(CO)82. Et2AlCl
[major]1, Bu3P
o-NO2-PhSeCN2. Davis’soxaziridine
stepsMe H
HO
O
MeMeH
1.BnOCHPP32.(EtO)2POCH2N
H
HO
MeMe
H
O
NC
OMeH
HO
MeMe
H
NC IMeMe
O
Me
Me
Me
H
Me H
H
H
H
1. HCl2. NaBH43. PPh3, I2
1. t-BuLi2. K/18-crown-6
O
OMe
Me
HH
OEt
OEt
A-1
p-TsOH
3-methyl-1,3-butanediol
Paquette, L. A. et al., JACS, 1997, 8438
Schreiber, S. L. et al., JACS, 1997, 4353
1. Tf2O, DTBMP
