Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes

Tereza Pavlíčková; Yannick Stöckl; Ilan Marek

doi:10.1021/acs.orglett.2c03756

Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes

Tereza Pavlíčková, Yannick Stöckl, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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

Abstract

Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters.

Original language	English
Pages (from-to)	8901-8906
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	48
DOIs	https://doi.org/10.1021/acs.orglett.2c03756
State	Published - 9 Dec 2022

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c03756

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abstract = "Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters.",

author = "Tereza Pavl{\'i}{\v c}kov{\'a} and Yannick St{\"o}ckl and Ilan Marek",

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AU - Pavlíčková, Tereza

AU - Stöckl, Yannick

AU - Marek, Ilan

PY - 2022/12/9

Y1 - 2022/12/9

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AB - Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters.

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U2 - 10.1021/acs.orglett.2c03756

DO - 10.1021/acs.orglett.2c03756

M3 - مقالة

C2 - 36446049

SN - 1523-7060

VL - 24

SP - 8901

EP - 8906

JO - Organic Letters

JF - Organic Letters

IS - 48

ER -

Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes

Abstract

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