Reductive diallylation of natural amino acids with triallylborane. The first synthesis of chiral 1,1,-diallyl-2-amino alcohols and their cyclization into optically active pyrrolidines.

✍ Scribed by Yuri N Bubnov; Mikhail A Misharin; Anatoly V Ignatenko

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 423 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01402-0

✦ Synopsis

The titled amino alcohols are obtained by treatment of chiral amino acids with triallylborane. Electrophylic iodocyclization of the alcohols leads to pyrrolidine derivatives. @ 1997 Elsevier Science Ltd.

Optically active 2-amino alcohols are widely used in organic synthesis as chiral inductors,l-3 building blocks,4 chiral reagents for the resolution of racemic acids and lactones,5 bases,6 and for the preparation of optically active organoboranes.7 (S)-Pyrrolidylmethanol (A), (S.)-1,1-diphenyl-l-pyrrolidylmethanol (B) and a number of chiral ~-arnino alcohols derived from ($)-valine (C) are used as catalysts for asymmetric reduction and alkylation of carbonyl compounds. 1~8