A novel gamma-selective conjugate addition of 1-silyl-substituted dienol ethers to nitroalkenes activated by Lewis acids has been developed. The resulting alpha,beta-unsaturated acylsilanes undergo photoinduced protodesilylation to afford the corresponding enals, which can be conveniently transformed into azepanes under appropriate reductive conditions.
Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes. Publishing Authors By Initials
Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes. Journal Published:
PUBLICATION TYPE: Research Support, N.I.H., Extr
Journal: The Journal of organic chemistry
VOLUME: 72
Page Numbers: 7050-3
Journal Abbreviation: J. Org. Chem.
ISSN: 0022-3263
DAY: 3
MONTH: 08
YEAR: 2007
Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes. Information
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LANGUAGE: eng
NlmUniqueID: 2985193
Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes. Keywords Mesh Terms:
KEYWORDS: Silanes
MESH TERMS: chemistry
Chemical & Substance for Abstract: Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes. Information
Substance Name: Silanes
Registry Number: 0
Grant and Affiliation Information for Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes.
AFFILIATION: Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Country: United States
AGENCY: United States NIGMS
GRANT: GM R01-30938
ACRONYM: GM
MEDLINETA: J Org Chem
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