Chiral synthesis via organoboranes. 11. Hydroboration. 82. Asymmetric hydroboration of 1-heteroarylcycloalkenes with monoisopinocampheylborane. Synthesis of …

HC Brown, AK Gupta, JVN Vara Prasad

Index: Brown, Hebert C.; Gupta, Ashok K.; Vara Prasad, J. V. N. Bulletin of the Chemical Society of Japan, 1988 , vol. 61, # 1 p. 93 - 100

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Citation Number: 12

Abstract

The hydroboration of representative 1-heteroarylcycloalkenes with monoisopinocampheylborane (IpcBH 2) was investigated systematically to establish the degree of asymmetric induction during hydroboration. The hydroboration of 1- heteroarylcyclopentene with IpcBH 2 at− 25° C proceeded cleanly to afford the corresponding dialkylboranes. These dialkylboranes, upon treatment with acetaldehyde ...