Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Δ(9(12))-capnellene

Takashi Ohshima; Katsuji Kagechika; Midori Adachi; Mikiko Sodeoka; Masakatsu Shibasaki

doi:10.1021/ja9609359

Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Δ(9(12))-capnellene

Takashi Ohshima, Katsuji Kagechika, Midori Adachi, Mikiko Sodeoka, Masakatsu Shibasaki

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

125 Citations (Scopus)

Abstract

An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.

Original language	English
Pages (from-to)	7108-7116
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	118
Issue number	30
DOIs	https://doi.org/10.1021/ja9609359
Publication status	Published - Jul 31 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja9609359

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abstract = "An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.",

author = "Takashi Ohshima and Katsuji Kagechika and Midori Adachi and Mikiko Sodeoka and Masakatsu Shibasaki",

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AU - Kagechika, Katsuji

AU - Adachi, Midori

AU - Sodeoka, Mikiko

AU - Shibasaki, Masakatsu

PY - 1996/7/31

Y1 - 1996/7/31

N2 - An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.

AB - An asymmetric Heck reaction-carbanion capture process was realized for the first time, making possible the catalytic asymmetric synthesis of various functionalized bicyclo[3.3.0]octane derivatives 6 in up to 94% ee. Sodium bromide had interesting effects on this asymmetric Heck reaction-carbanion capture process, and these effects were useful for improving the enantiomeric excess. Furthermore, the catalytic asymmetric synthesis of (-)-Δ(9(12))-capnellene (7) was achieved for the first time, using 6b as a key intermediate and a radical cyclization as a key step.

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Asymmetric Heck reaction-carbanion capture process. Catalytic asymmetric total synthesis of (-)-Δ(9(12))-capnellene

Abstract

All Science Journal Classification (ASJC) codes

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