Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers

Authors
Boeckman, RK Boehmler, DJ Musselman, RA
Citation
Rk. Boeckman et al., Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers, ORG LETT, 3(23), 2001, pp. 3777-3780
Citations number
56
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
23
Year of publication
2001
Pages
3777 - 3780
Database
ISI
SICI code
1523-7060(20011115)3:23<3777:TTDOAG>2.0.ZU;2-W
Abstract
[GRAPHICS] Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylat e with very high diastereoselectivity. A second alkylation occurs with reac tive alkylating agents to afford quaternary centers also with high diastere oselectivity, In accord with a proposed model for diastereoselection, lithi um and sodium enolates provide products with an opposite sense of asymmetri c induction.