Stereodivergent Hydroboration of Allenes

Yoshiyuki Nagashima; Keiji Sasaki; Takahiro Suto; Takaaki Sato; Noritaka Chida

doi:10.1002/asia.201800134

Stereodivergent Hydroboration of Allenes

Yoshiyuki Nagashima, Keiji Sasaki, Takahiro Suto, Takaaki Sato, Noritaka Chida

Department of Applied Chemistry

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

22 Citations (Scopus)

Abstract

Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)₂ (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

Original language	English
Pages (from-to)	1024-1028
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	13
Issue number	8
DOIs	https://doi.org/10.1002/asia.201800134
Publication status	Published - 2018 Apr 16

Keywords

allenes
hydroboration
natural products
skipped dienes
stereoselectivity

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.201800134

Cite this

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abstract = "Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.",

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AU - Nagashima, Yoshiyuki

AU - Sasaki, Keiji

AU - Suto, Takahiro

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2018/4/16

Y1 - 2018/4/16

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AB - Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.

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Stereodivergent Hydroboration of Allenes

Abstract

Keywords

ASJC Scopus subject areas

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