Asymmetric synthesis of alpha-substituted beta-formyl delta-lactones via aMichael addition/alpha-alkylation protocol

Authors
Enders, D Vazquez, J
Citation
D. Enders et J. Vazquez, Asymmetric synthesis of alpha-substituted beta-formyl delta-lactones via aMichael addition/alpha-alkylation protocol, SYNLETT, (5), 1999, pp. 629-631
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
5
Year of publication
1999
Pages
629 - 631
Database
ISI
SICI code
0936-5214(199905):5<629:ASOABD>2.0.ZU;2-N
Abstract
An efficient trans-diastereo- and enantioselective synthesis of alpha-subst ituted beta-formyl delta-lactones 5 (de greater than or equal to 98%, ee = 80-95%) is described, employing formaldehyde-SAMP-hydrazone (1) as a neutra l formyl anion equivalent. The new procedure involves the Michael addition of 1 to 5,6-dihydro-2H-pyran- Zone (2) followed by trans-selective alpha-al kylation and subsequent oxidative cleavage of the auxiliary.