A pinene-based chiral auxiliary for alpha-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity

Authors
Pinheiro, S Goncalves, CBSS de Lima, MB de Farias, FMC
Citation
S. Pinheiro et al., A pinene-based chiral auxiliary for alpha-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity, TETRAHEDR-A, 11(17), 2000, pp. 3495-3502
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
17
Year of publication
2000
Pages
3495 - 3502
Database
ISI
SICI code
0957-4166(20000908)11:17<3495:APCAFA>2.0.ZU;2-A
Abstract
While the use of LDA as the base in the kinetic deprotonation step of the p inene-based ester 3 led to moderate diastereoselectivities in alpha -alkyla tion and aldol reactions, the use of LICA and LTMP resulted in a reduction in the anti/syn ratios and pi -facial selectivities. (C) 2000 Elsevier Scie nce Ltd. All rights reserved.