Enantioselective syntheses of ring-C precursors of vitamin B12. Substrate control. A novel Si-assisted elimination of vinyl bromides

Peter A Jacobi; Carlos Tassa

doi:10.1021/ol036061u

Enantioselective syntheses of ring-C precursors of vitamin B12. Substrate control. A novel Si-assisted elimination of vinyl bromides

Org Lett. 2003 Dec 11;5(25):4879-82. doi: 10.1021/ol036061u.

Authors

Peter A Jacobi¹, Carlos Tassa

Affiliation

¹ Burke Chemical Laboratory, Dartmouth College, Hanover, New Hampshire 03755, USA. peter.a.jacobi@dartmouth.edu

PMID: 14653697
DOI: 10.1021/ol036061u

Abstract

Homochiral ring-C precursors 34 of Vitamin B(12) have been prepared by Ireland-Claisen rearrangement of allyl esters 32, followed by a novel Si-assisted elimination of HBr. [reaction: see text]

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Bromides / chemistry*
Molecular Structure
Silicon / chemistry*
Stereoisomerism
Vitamin B 12 / analogs & derivatives*
Vitamin B 12 / chemical synthesis*
Vitamin B 12 / chemistry

Substances

Bromides
Vitamin B 12
Silicon

Grants and funding

GM 38913/GM/NIGMS NIH HHS/United States