Enantioselective Synthesis of Deoxymannojirimycin Based on Sharpless Asymmetric Epoxidation of a Highly Functionalized Allylic Alcohol | Zendy

Lamas MarieCéline | Zendy; Malacria Max | Zendy; Thorimbert Serge | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research