ChemInform Abstract: Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions....
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ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de Aziridine derivatives R 0040 Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions. Syn- thesis of Optically Pure trans-Aziridines. — LiN(Tms) 2 -mediated treatment of the sulfonium salt (I) with sulfinylimines results in stereoselective formation of aziridines. With (R)-sulfinylimines moderate cis/trans-selectivity and excellent facial diastereose- lectivity is achieved, while with (S)-sulfinylimines excellent trans-selectivity but low facial diastereoselectivity is observed. The reaction mainly proceeds via planar free carbanion which has strong influence on the stereoselective outcome. — (ARROYO, Y.; MEANA, A.; RODRIGUEZ, J. F.; SANZ-TEJEDOR*, M. A.; ALONSO, I.; GARCIA RUANO, J. L.; J. Org. Chem. 74 (2009) 11, 4217-4224; Dep. Quim. Org., Fac. Cienc., Univ. Valladolid, E-47011 Valladolid, Spain; Eng.) — Jannicke 43- 108
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Transcript of ChemInform Abstract: Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions....
www.cheminform.wiley-vch.de
Aziridine derivativesR 0040 Stereoselective Control of Planar α-Dimethylsulfonium Benzyl Carbanions. Syn-
thesis of Optically Pure trans-Aziridines. — LiN(Tms)2-mediated treatment of the sulfonium salt (I) with sulfinylimines results in stereoselective formation of aziridines. With (R)-sulfinylimines moderate cis/trans-selectivity and excellent facial diastereose-lectivity is achieved, while with (S)-sulfinylimines excellent trans-selectivity but low facial diastereoselectivity is observed. The reaction mainly proceeds via planar free carbanion which has strong influence on the stereoselective outcome. — (ARROYO, Y.; MEANA, A.; RODRIGUEZ, J. F.; SANZ-TEJEDOR*, M. A.; ALONSO, I.; GARCIA RUANO, J. L.; J. Org. Chem. 74 (2009) 11, 4217-4224; Dep. Quim. Org., Fac. Cienc., Univ. Valladolid, E-47011 Valladolid, Spain; Eng.) — Jannicke
43- 108
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cheminform.wiley-vch.de
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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