Abstract
Efficient syntheses of (2S,3S)-methylproline ( 5a) and (2S,3R)-phenylproline ( 5b) are described, starting from the readily available pyroglutaminol derivatives 2a and 2b via conjugate 1,4-addition of organocuprates to 1. Catalytic hydrogenation of 3 from the least hindered α-side furnishes 6, which is transformed to (2S,3R)-methylproline ( 7). 3-Substituted glutamic acids 8c, d are provided by a four step procedure from 2c, d.
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