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Substrate‐Assisted, Transition‐Metal‐Free Diboration of Alkynamides with Mixed Diboron: Regio‐ and Stereoselective Access to trans ‐1,2‐Vinyldiboronates
Author(s) -
Verma Astha,
Snead Russell F.,
Dai Yumin,
Slebodnick Carla,
Yang Yinuo,
Yu Haizhu,
Yao Fu,
Santos Webster L.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700946
Subject(s) - stereoselectivity , substrate (aquarium) , chemistry , transition metal , regioselectivity , metal , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , oceanography , geology
A substrate‐assisted diboration of alkynamides using the unsymmetrical pinacolato‐1,8‐diaminonaphthalenato diboron (pinBBdan) is described. The transition‐metal‐free reaction proceeds in a regio‐ and stereoselective fashion to exclusively afford trans ‐vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α‐ and β‐carbon atoms, respectively.