ACID-CATALYZED REARRANGEMENT OF ALPHA-HYDROXYCYCLOPROPYLSILANES

Acidic treatment of the (1S,1'S,2'R)-alpha-hydroxycyclopropylsilane 1 gave a mixture of rearranged products, which were composed of the ring -opened (S)-vinylsilane 3, the tandem [1,2]-CC bond migration product (1S,2R,1'S)-silylcyclopropane 4, and its 1'R isomer 5, respectively. H ence, the use of the 2'S isomer 2 produced a mixture of the (R)-3, 4, and 5, Our proposed mechanisms of the present cationic rearrangement a re also described. (C) 1998 Elsevier Science Ltd. All rights reserved.