GRIGNARD ADDITIONS TO ALPHA,BETA-UNSATURATED DIOXOLANONES - PREPARATION OF CHIRAL ALLYLIC ALCOHOLS AND PROTECTED ALPHA-HYDROXY ALDEHYDES

Authors
HECKMANN B MIOSKOWSKI C BHATT RK FALCK JR
Citation
B. Heckmann et al., GRIGNARD ADDITIONS TO ALPHA,BETA-UNSATURATED DIOXOLANONES - PREPARATION OF CHIRAL ALLYLIC ALCOHOLS AND PROTECTED ALPHA-HYDROXY ALDEHYDES, Tetrahedron letters, 37(9), 1996, pp. 1421-1424
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
9
Year of publication
1996
Pages
1421 - 1424
Database
ISI
SICI code
0040-4039(1996)37:9<1421:GATAD->2.0.ZU;2-E
Abstract
alpha,beta-Unsaturated dioxolanones derived from mandelic acid smoothl y add most Grignard reagents with good to excellent regio- and diaster eoselectivities. The adducts are converted to chiral secondary alcohol s by peroxidation at low temperature or to protected alpha-hydroxy ald ehydes via ozonolysis.