Generation of (E)-silylketene acetals in a Rhodium-DuPhos catalyzed two-step reductive aldol reaction

Authors
Zhao, CX Bass, J Morken, JP
Citation
Cx. Zhao et al., Generation of (E)-silylketene acetals in a Rhodium-DuPhos catalyzed two-step reductive aldol reaction, ORG LETT, 3(18), 2001, pp. 2839-2842
Citations number
61
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
18
Year of publication
2001
Pages
2839 - 2842
Database
ISI
SICI code
1523-7060(20010906)3:18<2839:GO(AIA>2.0.ZU;2-A
Abstract
Mechanistic studies employing in situ NMR analysis implicate intermediate s ilicon enolates as reactive intermediates in the Rh-DuPhos catalyzed two-st ep reductive aldol reaction with Cl2MeSiH. These enolates undergo noncataly zed reaction with a variety of aldehydes to give the derived syn-aldol addu ct in high yields and diastereoselection.