Bulletin of the Chemical Society of Japan p. 1393 - 1401 (1997)
Update date:2022-08-03
Topics:
Kobayashi, Kimiko
Kato, Takayuki
Unno, Masafumi
Masuda, Shinji
Optically active silanes were synthesized by a novel asymmetric synthesis which involved the diastereoselective ring-opening reaction of 1,3-dioxa-2-silacycloheptanes bearing a C2 chiral auxiliary with Grignard reagents, followed by a lithium aluminum hydride (LiAlH4) reduction. (R)-Ethylmethylphenylsilane and (R)-methylphenylpropylsilane were derived in 93%ee and 98%ee, respectively. The preparation of the other optical silanes is also described. The maximum rotations of some of them have been determined by 1H NMR and/or capillary GC methods. A mechanism for a diastereoselective ring-opening reaction is proposed based on the stereochemical results.
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Doi:10.1016/S0040-4039(00)77685-4
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(1997)