Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane

Songjie Yu; Caizhi Wu; Shaozhong Ge

doi:10.1021/jacs.7b01708

Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane

Songjie Yu
, Caizhi Wu
, Shaozhong Ge^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

170 Citations (Scopus)

Abstract

We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac) ₂ and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86%-99% ee).

Original language	English
Pages (from-to)	6526-6529
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	19
Early online date	4 May 2017
DOIs	https://doi.org/10.1021/jacs.7b01708
Publication status	Published - 17 May 2017

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title = "Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane",

abstract = " We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac) 2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86\%-99\% ee). ",

author = "Songjie Yu and Caizhi Wu and Shaozhong Ge",

year = "2017",

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doi = "10.1021/jacs.7b01708",

language = "English",

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journal = "Journal of the American Chemical Society",

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T1 - Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane

AU - Yu, Songjie

AU - Wu, Caizhi

AU - Ge, Shaozhong

PY - 2017/5/17

Y1 - 2017/5/17

N2 - We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac) 2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86%-99% ee).

AB - We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac) 2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86%-99% ee).

UR - https://www.scopus.com/pages/publications/85019647073

U2 - 10.1021/jacs.7b01708

DO - 10.1021/jacs.7b01708

M3 - Article (Academic Journal)

C2 - 28449577

AN - SCOPUS:85019647073

SN - 0002-7863

VL - 139

SP - 6526

EP - 6529

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 19

ER -

Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane

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