Stereoselective Synthesis of Polysubstituted Spiropentanes

Yair Cohen; Dor Toledano; Ilan Marek

doi:10.1021/jacs.2c07370

Stereoselective Synthesis of Polysubstituted Spiropentanes

Yair Cohen, Dor Toledano, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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

Abstract

A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp 2-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.

Original language	English
Pages (from-to)	16732-16736
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	144
Issue number	37
DOIs	https://doi.org/10.1021/jacs.2c07370
State	Published - 11 Sep 2022

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10.1021/jacs.2c07370

https://pubs.acs.org/doi/10.1021/jacs.2c07370

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title = "Stereoselective Synthesis of Polysubstituted Spiropentanes",

abstract = "A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp 2-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters. ",

author = "Yair Cohen and Dor Toledano and Ilan Marek",

year = "2022",

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doi = "10.1021/jacs.2c07370",

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journal = "Journal of the American Chemical Society",

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AU - Toledano, Dor

AU - Marek, Ilan

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Y1 - 2022/9/11

N2 - A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp 2-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.

AB - A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp 2-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.

U2 - 10.1021/jacs.2c07370

DO - 10.1021/jacs.2c07370

M3 - مقالة

C2 - 36088586

SN - 0002-7863

VL - 144

SP - 16732

EP - 16736

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 37

ER -

Stereoselective Synthesis of Polysubstituted Spiropentanes

Abstract

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