Chemistry–A European Journal

Highly Stereoselective Iodolactonization of 4, 5??Allenoic Acids—An Efficient Synthesis of 5??(1′??Iodo??1′(Z)??alkenyl)??4, 5??dihydro??2 (3H)??furanones

X Jiang, C Fu, S Ma

Index: Jiang, Xinpeng; Fu, Chunling; Ma, Shengming Chemistry - A European Journal, 2008 , vol. 14, # 31 p. 9656 - 9664

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Citation Number: 28

Abstract

Abstract In this paper, it is reported that the efficient iodolactonization of 4, 5-allenoic acid with I 2 in cyclohexane in the presence or absence of K 2 CO 3 afforded 5-(1′-iodo-1′(Z)- alkenyl)-4, 5-dihydro-2 (3H)-furanones highly stereoselectively. However, the reaction of axially optically active 4, 5-allenoic acids (R)-(−)-5 a and (R)-(−)-5 b with I 2 afforded the corresponding products with a serious loss of chirality. This problem was solved by ...