Highly Diastereoselective and Enantioselective Preparation of Homoallylic Amines: Application for the Synthesis of β??Amino Acids and γ??Lactams

PV Ramachandran, TE Burghardt

Index: Ramachandran, P. Veeraraghavan; Burghardt, Thomas E. Chemistry - A European Journal, 2005 , vol. 11, # 15 p. 4387 - 4395

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Citation Number: 55

Abstract

Abstract Reactions of N-silyl-and N-aluminoimines with B-allyldiisopinocampheylborane in the presence of methanol, followed by oxidative workup furnished homoallylic amines in good yields and high ee. A 11 B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of ...

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