[reaction: see text] We report the catalytic asymmetric allylation of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantioselectivities (79-95%). The resulting homoallylic alcohols can also be epoxidized in situ using tert-butyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).
Highly concentrated catalytic asymmetric allylation of ketones. Publishing Authors By Initials
Highly concentrated catalytic asymmetric allylation of ketones. Journal Published:
PUBLICATION TYPE: Research Support, N.I.H., Extr
Journal: Organic letters
VOLUME: 9
Page Numbers: 381-4
Journal Abbreviation: Org. Lett.
ISSN: 1523-7060
DAY: 1
MONTH: Feb
YEAR: 2007
Highly concentrated catalytic asymmetric allylation of ketones. Information
Number of References:
LANGUAGE: eng
NlmUniqueID: 100890393
Highly concentrated catalytic asymmetric allylation of ketones. Keywords Mesh Terms:
KEYWORDS: tert-Butylhydroperoxide
MESH TERMS: chemistry
Chemical & Substance for Abstract: Highly concentrated catalytic asymmetric allylation of ketones. Information
Substance Name: tert-Butylhydroperoxide
Registry Number: 75-91-2
Grant and Affiliation Information for Highly concentrated catalytic asymmetric allylation of ketones.
AFFILIATION: P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Country: United States
AGENCY: United States NIGMS
GRANT: GM58101
ACRONYM: GM
MEDLINETA: Org Lett
REFSOURCE:
DATABASENAME:
ACCESSION NUMBER:
Number Hits: 0
Highly concentrated catalytic asymmetric allylation of ketones Related Publications