Back to Search Start Over

An efficient synthesis of α-methylene-γ-butyrolactones from Baylis–Hillman adducts via an In-mediated Barbier reaction and stereoselective lactonization under MeSO2Cl/Et3N conditions

Authors :
Ko Hoon Kim
Jae Nyoung Kim
Bo Ram Park
Source :
Tetrahedron Letters. 51:6568-6571
Publication Year :
2010
Publisher :
Elsevier BV, 2010.

Abstract

An efficient synthesis of trans -α-methylene-γ-butyrolactones is disclosed from syn -homoallylic alcohols via the intramolecular mesylate displacement reaction promoted by nearby ester group under the influence of MsCl/Et 3 N. syn -Homoallylic alcohols were prepared via the In-mediated Barbier reaction of the bromides of Baylis–Hillman adducts.

Details

ISSN :
00404039
Volume :
51
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........083ece43cfc770009afa445db8f60e06
Full Text :
https://doi.org/10.1016/j.tetlet.2010.10.077