Organoboranes. 38. A facile and highly efficient addition of B-1-alkynyl-9-borabicyclo [3.3. 1] nonanes to aldehydes and ketones: an exceptionally chemoselective …

…, GA Molander, SM Singh, US Racherla

Index: Brown, Herbert C.; Molander, Gary A.; Singh, Shankar M.; Racherla, Uday S. Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1577 - 1582

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Citation Number: 46

Abstract

Bl-Alkynyl-9-borabicyclo [3.3. l] nonanes (B-1-alkynyl-9-BBN) readily undergo addition to aldehydes and ketones and afford the propargylic alcohols in very high isolated yields. Unlike many other alkynyl metals (RC= CM, M= Li, Na, K, Mg, Zn, and Al), which are highly reactive toward various functional groups, E-alkynyl-9-BBN compounds are exceptionally mild and react with unhindered aldehydes in the presence of ketones with a remarkable ...

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