Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot

Akihiro Orita; Akihiro Watanabe; Hiroshi Tsuchiya; Junzo Otera

doi:10.1016/S0040-4020(99)00053-8

Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot

Akihiro Orita, Akihiro Watanabe, Hiroshi Tsuchiya, Junzo Otera

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

24 Citations (Scopus)

Abstract

According to 'integrated chemical process', a novel one-pot process for construction of highly substituted allylic moieties has been achieved. A series of alkylation of allylic sulfones and palladium-catalyzed reductive desulfonylation by use of LiBHEt₃ is integrated. The double alkylation furnishes more substituted olefins. Use of arylzinc compounds in place of the hydride enables electrophilic alkylation/nucleophilic arylation in one-pot. The integrated process provides higher overall yields than the corresponding stepwise process.

Original language	English
Pages (from-to)	2889-2898
Number of pages	10
Journal	Tetrahedron
Volume	55
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4020(99)00053-8
Publication status	Published - Mar 5 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(99)00053-8

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title = "Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot",

abstract = "According to 'integrated chemical process', a novel one-pot process for construction of highly substituted allylic moieties has been achieved. A series of alkylation of allylic sulfones and palladium-catalyzed reductive desulfonylation by use of LiBHEt3 is integrated. The double alkylation furnishes more substituted olefins. Use of arylzinc compounds in place of the hydride enables electrophilic alkylation/nucleophilic arylation in one-pot. The integrated process provides higher overall yields than the corresponding stepwise process.",

author = "Akihiro Orita and Akihiro Watanabe and Hiroshi Tsuchiya and Junzo Otera",

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AU - Orita, Akihiro

AU - Watanabe, Akihiro

AU - Tsuchiya, Hiroshi

AU - Otera, Junzo

N1 - Funding Information: Acknowledgment. This work was supported by The Japan Society for the Promotion of Science under "Research for the Future" Program (JSPS-PFTF96P00303).

PY - 1999/3/5

Y1 - 1999/3/5

N2 - According to 'integrated chemical process', a novel one-pot process for construction of highly substituted allylic moieties has been achieved. A series of alkylation of allylic sulfones and palladium-catalyzed reductive desulfonylation by use of LiBHEt3 is integrated. The double alkylation furnishes more substituted olefins. Use of arylzinc compounds in place of the hydride enables electrophilic alkylation/nucleophilic arylation in one-pot. The integrated process provides higher overall yields than the corresponding stepwise process.

AB - According to 'integrated chemical process', a novel one-pot process for construction of highly substituted allylic moieties has been achieved. A series of alkylation of allylic sulfones and palladium-catalyzed reductive desulfonylation by use of LiBHEt3 is integrated. The double alkylation furnishes more substituted olefins. Use of arylzinc compounds in place of the hydride enables electrophilic alkylation/nucleophilic arylation in one-pot. The integrated process provides higher overall yields than the corresponding stepwise process.

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Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot

Abstract

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