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Stereodivergent Hydroboration of Allenes
Author(s) -
Nagashima Yoshiyuki,
Sasaki Keiji,
Suto Takahiro,
Sato Takaaki,
Chida Noritaka
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800134
Subject(s) - hydroboration , allene , chemistry , stereoselectivity , allylic rearrangement , natural product , allylic alcohol , stereochemistry , organic chemistry , catalysis
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.