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

^*此作品的通讯作者

CAS - Shanghai Institute of Organic Chemistry
Chinese University of Hong Kong

科研成果: 期刊稿件 › 文章 › 同行评审

86 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	13151-13154
页数	4
期刊	Journal of the American Chemical Society
卷	138
期	40
DOI	https://doi.org/10.1021/jacs.6b08279
出版状态	已出版 - 12 10月 2016
已对外发布	是

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@article{a3481b32db2940b19c19912fb4700aaa,

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",

language = "英语",

volume = "138",

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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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