Chiral synthesis via organoboranes. 48. Efficient synthesis of trans-fused bicyclic and cyclic ketones and secondary alcohols in high optical purities via asymmetric …

UP Dhokte, PM Pathare, VK Mahindroo…

文献索引：Dhokte, Ulhas P.; Pathare, Pradip M.; Mahindroo, Verinder K.; Brown, Herbert C. Journal of Organic Chemistry, 1998 , vol. 63, # 23 p. 8276 - 8283

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被引用次数: 14

摘要

Highly stereo-and enantioselective annelation has been achieved for the synthesis of trans- fused bicyclic and cyclic ketones via the asymmetric cyclic hydroboration of suitable cyclic dienes, such as 1-allyl-1-cycloalkenes or 1-vinyl-1-cycloalkenes and appropriate acyclic 1, 4- dienes, respectively, with enantiomerically pure isopinocampheylchloroborane etherate (IpcBHCl⊙ Et2O). The IpcBHCl⊙ Et2O (an 86-90% equilibrium mixture) was readily ...