Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.
N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes. Publishing Authors By Initials
N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes. Journal Published:
PUBLICATION TYPE: Research Support, U.S. Gov't,
Journal: Organic letters
VOLUME: 9
Page Numbers: 2581-4
Journal Abbreviation: Org. Lett.
ISSN: 1523-7060
DAY: 1
MONTH: 06
YEAR: 2007
N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes. Information
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LANGUAGE: eng
NlmUniqueID: 100890393
N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes. Keywords Mesh Terms:
KEYWORDS: Silanes
MESH TERMS: chemistry
Chemical & Substance for Abstract: N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes. Information
Substance Name: Silanes
Registry Number: 0
Grant and Affiliation Information for N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.
AFFILIATION: Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Country: United States
AGENCY: United States NIGMS
GRANT: R01 GM073072
ACRONYM: GM
MEDLINETA: Org Lett
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