Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B

Jiang Lin Hu; Liang Wen Feng; Lijia Wang; Zuowei Xie; Yong Tang; Xiaoge Li

doi:10.1021/jacs.6b08279

Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B

Jiang Lin Hu, Liang Wen Feng, Lijia Wang, Zuowei Xie, Yong Tang, Xiaoge Li

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

81 Scopus citations

Abstract

A highly diastereoselective and enantioselective Cu(II)/SaBOX-catalyzed [2 + 2] cycloaddition of methylidenemalonate and multisubstituted alkenes was developed to furnish optically active cyclobutanes in high yields with >99/1 dr and up to >99% ee. By application of the newly developed method, the total synthesis of (+)-piperarborenine B was completed in eight steps from methylidenemalonate and olefin in 17% overall yield with >99/1 dr and 99% ee.

Original language	English
Pages (from-to)	13151-13154
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	40
DOIs	https://doi.org/10.1021/jacs.6b08279
State	Published - 12 Oct 2016
Externally published	Yes

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title = "Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B",

abstract = "A highly diastereoselective and enantioselective Cu(II)/SaBOX-catalyzed [2 + 2] cycloaddition of methylidenemalonate and multisubstituted alkenes was developed to furnish optically active cyclobutanes in high yields with >99/1 dr and up to >99\% ee. By application of the newly developed method, the total synthesis of (+)-piperarborenine B was completed in eight steps from methylidenemalonate and olefin in 17\% overall yield with >99/1 dr and 99\% ee.",

author = "Hu, \{Jiang Lin\} and Feng, \{Liang Wen\} and Lijia Wang and Zuowei Xie and Yong Tang and Xiaoge Li",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = oct,

day = "12",

doi = "10.1021/jacs.6b08279",

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volume = "138",

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journal = "Journal of the American Chemical Society",

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T1 - Enantioselective Construction of Cyclobutanes

T2 - A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B

AU - Hu, Jiang Lin

AU - Feng, Liang Wen

AU - Wang, Lijia

AU - Xie, Zuowei

AU - Tang, Yong

AU - Li, Xiaoge

PY - 2016/10/12

Y1 - 2016/10/12

N2 - A highly diastereoselective and enantioselective Cu(II)/SaBOX-catalyzed [2 + 2] cycloaddition of methylidenemalonate and multisubstituted alkenes was developed to furnish optically active cyclobutanes in high yields with >99/1 dr and up to >99% ee. By application of the newly developed method, the total synthesis of (+)-piperarborenine B was completed in eight steps from methylidenemalonate and olefin in 17% overall yield with >99/1 dr and 99% ee.

AB - A highly diastereoselective and enantioselective Cu(II)/SaBOX-catalyzed [2 + 2] cycloaddition of methylidenemalonate and multisubstituted alkenes was developed to furnish optically active cyclobutanes in high yields with >99/1 dr and up to >99% ee. By application of the newly developed method, the total synthesis of (+)-piperarborenine B was completed in eight steps from methylidenemalonate and olefin in 17% overall yield with >99/1 dr and 99% ee.

UR - https://www.scopus.com/pages/publications/84991294607

U2 - 10.1021/jacs.6b08279

DO - 10.1021/jacs.6b08279

M3 - 文章

AN - SCOPUS:84991294607

SN - 0002-7863

VL - 138

SP - 13151

EP - 13154

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 40

ER -

Enantioselective Construction of Cyclobutanes: A New and Concise Approach to the Total Synthesis of (+)-Piperarborenine B

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