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

56 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.\}",

year = "1988",

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

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volume = "29",

pages = "6693--6696",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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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.

UR - https://www.scopus.com/pages/publications/45549111473

UR - https://www.scopus.com/pages/publications/45549111473#tab=citedBy

U2 - 10.1016/S0040-4039(00)82430-2

DO - 10.1016/S0040-4039(00)82430-2

M3 - Article

AN - SCOPUS:45549111473

SN - 0040-4039

VL - 29

SP - 6693

EP - 6696

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

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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