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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 5
BKCSDE 8(5)
May 20, 1987

Title	Enantioselective Reduction of Racemic Three-Membered Heterocyclic Compounds. 3. Reaction of Epoxides with B-Isopinocampheyl-9-borabicycolo[3.3.1]nonane-Potassium Hydride and Potassium B-Isopinocampheyl-9 boratabicyclo[3.3.1]nonane Systems1
Author	Jin Soon Cha*, Kwang Woo Lee, Nung Min Yoon
Keywords
Abstract	The chiral B-isopinocampheyl-9-borabicyclo[3.3.1]nonane-pot assium hydride (IPC-9-BBN-KH) and potassium B-isopinocampheyl-9-boratabicyclo[3.3.1]nonane (K IPC-9-BBNH) systems were applied to the enantioselective reduction of representative racemic epoxides, namely 1,2-epoxybutane, 1,2-epoxyoctane, 3,3-dimethyl-1,2-epoxybutane and styrene oxide. In the case of IPC-9-BBN-KH system, the optical yields are in the range of 8.3-37.4% ee. However, the system of K IPC-9-BBNH provides significantly lower optical yields, showing 7-22.5% ee. These results strongly suggest that the enantioselective coordination of chiral organoborane to the epoxy oxygen of racemic epoxides plays an important role in this resolution
Page	421 - 423
Full Text	PDF

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