The Journal of Organic Chemistry

Selective propargylation of carbonyl compounds with allenylstannane/alkyllithium mixed reagents

M Suzuki, Y Morita, R Noyori

Index: Suzuki, Masaaki; Morita, Yasushi; Noyori, Ryoji Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 441 - 449

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Citation Number: 47

Abstract

1-Substituted allenyltrialkylstannanes readily undergo transmetalation with an alkyllithium to generate a tetraalkylstannane and an equilibrating mixture of the allenyl-and propargyllithium compounds. The organolithium derivatives react with a variety of aldehydes and ketones at low temperature to give, after aqueous workup, the regioisomeric acetylenic and allenic carbinols in high yields. The degree of the regioselection is highly sensitive to ...