1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction

Ming Chang P. Yeh; Paul Knochel; William M. Butler; Scott C. Berk

doi:10.1016/S0040-4039(00)82430-2

1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP₃ to trisubstituted enones. A new BF₃ promoted cyclization reaction

Ming Chang P. Yeh^*, Paul Knochel, William M. Butler, Scott C. Berk

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

51 Citations (Scopus)

Abstract

The new copper reagents RCu(CN)Zn I · 2 BF₃ 1 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4-7 in high yields (81-98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a-11c which could be converted into the bicyclic diketones 12 under mild basic conditions. The X-ray structure of 11b is reported.

Original language	English
Pages (from-to)	6693-6696
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)82430-2
Publication status	Published - 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction",

abstract = "The new copper reagents RCu(CN)Zn I · 2 BF3 1 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4-7 in high yields (81-98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a-11c which could be converted into the bicyclic diketones 12 under mild basic conditions. The X-ray structure of 11b is reported.",

author = "Yeh, {Ming Chang P.} and Paul Knochel and Butler, {William M.} and Berk, {Scott C.}",

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doi = "10.1016/S0040-4039(00)82430-2",

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T1 - 1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction

AU - Yeh, Ming Chang P.

AU - Knochel, Paul

AU - Butler, William M.

AU - Berk, Scott C.

PY - 1988

Y1 - 1988

N2 - The new copper reagents RCu(CN)Zn I · 2 BF3 1 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4-7 in high yields (81-98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a-11c which could be converted into the bicyclic diketones 12 under mild basic conditions. The X-ray structure of 11b is reported.

AB - The new copper reagents RCu(CN)Zn I · 2 BF3 1 containing various functional groups like esters, cyanides, chlorides or enoates react with β, β′- disubstituted enones to afford the Michael adducts 4-7 in high yields (81-98%). Cyano-substituted 1,4-adducts undergo a new cyclization reaction leading to the very stable bicyclic difluoroboron enolates 11a-11c which could be converted into the bicyclic diketones 12 under mild basic conditions. The X-ray structure of 11b is reported.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP₃ to trisubstituted enones. A new BF₃ promoted cyclization reaction

Abstract

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