DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL ALDEHYDES AND CHIRAL METHYL KETONES - DEPENDENCE OF STEREOSELECTIVITY ON THE METAL ENOLATE, THE ALDEHYDE 2,3-STEREOCHEMISTRY, AND THE ALDEHYDE BETA-ALKOXY PROTECTING GROUP

Authors
GUSTIN DJ VANNIEUWENHZE MS ROUSH WR
Citation
Dj. Gustin et al., DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL ALDEHYDES AND CHIRAL METHYL KETONES - DEPENDENCE OF STEREOSELECTIVITY ON THE METAL ENOLATE, THE ALDEHYDE 2,3-STEREOCHEMISTRY, AND THE ALDEHYDE BETA-ALKOXY PROTECTING GROUP, Tetrahedron letters, 36(20), 1995, pp. 3443-3446
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
20
Year of publication
1995
Pages
3443 - 3446
Database
ISI
SICI code
0040-4039(1995)36:20<3443:DAROCA>2.0.ZU;2-7
Abstract
The stereoselectivity of aldol reactions of chiral aldehydes 5 and 11 with methyl ketone enolates is highly dependent on the aldehyde 2,3-st ereochemistry, the aldehyde beta-alkoxy protecting group, and the meta l enolate. The selectivity trends are rationalized by a competition be tween chair-like and boat-like transition states.