ChemInform Abstract: The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis...

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1999 addition reactions addition reactions O 0060 25 - 036 The Nitro-Mannich Reaction and Its Application to the Stereos- elective Synthesis of 1,2-Diamines. Alkyl nitronate anions react with Pmb-imines (II) in the presence of Broensted acid to give β-nitro amines. In most cases, a high anti-selectivity up to 10:1 is observed. The moderately stable products (III) can be easily reduced and then deprotected with CAN to yield the diamines (VI) without erosion of diastereoselectivity. — (ADAMS, HARRY; ANDERSON, JAMES C.; PEACE, SIMON; PENNELL, ANDREW M. K.; J. Org. Chem. 63 (1998) 26, 9932-9934; Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK; EN) 1

Transcript of ChemInform Abstract: The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis...

Page 1: ChemInform Abstract: The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis of 1,2-Diamines.

1999 addition reactions

addition reactionsO 0060

25 - 036The Nitro-Mannich Reaction and Its Application to the Stereos-elective Synthesis of 1,2-Diamines. — Alkyl nitronate anions reactwith Pmb-imines (II) in the presence of Broensted acid to give β-nitro amines.In most cases, a high anti-selectivity up to 10:1 is observed. The moderatelystable products (III) can be easily reduced and then deprotected with CAN toyield the diamines (VI) without erosion of diastereoselectivity. — (ADAMS,HARRY; ANDERSON, JAMES C.; PEACE, SIMON; PENNELL, ANDREWM. K.; J. Org. Chem. 63 (1998) 26, 9932-9934; Dep. Chem., Univ. Sheffield,Sheffield S3 7HF, UK; EN)

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