Selective monoacylation of symmetrical diamines via prior complexation with boron.
[reaction: see text] Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.
Zhang
Zhongxing
Z
Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
Yin
Zhiwei
Z
Meanwell
Nicholas A
NA
Kadow
John F
JF
Wang
Tao
T