A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine

作者：Stead Darren; O'Brien Peter^*; Sanderson Adam

来源：Organic Letters, 2008, 10(7): 1409-1412.

DOI：10.1021/ol800109s

The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The (S,S)-diamine is a useful (+)sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.

• 出版日期2008-4-3