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Enantioselective Synthesis of Deoxymannojirimycin Based on Sharpless Asymmetric Epoxidation of a Highly Functionalized Allylic Alcohol
Author(s) -
Lamas MarieCéline,
Malacria Max,
Thorimbert Serge
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100102
Subject(s) - enantioselective synthesis , chemistry , piperidine , allylic rearrangement , enantiomer , stereoselectivity , intramolecular force , sharpless epoxidation , stereochemistry , alcohol , allylic alcohol , organic chemistry , catalysis
An efficient enantioselective synthesis of deoxymannojirimicin is reported. It is based on the unusual Sharpless asymmetric epoxidation of a silyl‐substituted allylic 1,4‐amino alcohol coupled with a further highly stereoselective intramolecular aldolization. Both enantiomers of deoxymannojirimicin are available. An orthogonally protected polyhydroxylated piperidine was prepared, which could formally lead to other members of this piperidine family.