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Rh-Catalyzed Enantioselective Allylation of N-Tosyl- And N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Rh-Catalyzed Enantioselective Allylation of N-Tosyl- And N-Nosylaldimines: Total Synthesis of (-)-Crispine A

Pei-Fen Chiang, Wei-Sian Li, Jia-Hong Jian, Ting-Shen Kuo, Ping-Yu Wu, Hsyueh-Liang Wu

Org Lett. 2018 Jan 5;20(1):158-161.

PMID: 29257696

Abstract:

The unprecedented development of asymmetric Rh-catalyzed 1,2-allylation of N-Ts- and N-Ns-aldimines is achieved. This protocol utilizes potassium allyltrifluoroborates and various aldimines to generate enantioenriched homoallylic amines in the presence of 3.0 mol % of Rh(I)/L1b catalyst with up to 90% yield, 98% ee (R = H), and 10:1 diastereoselectivity (R = Me or Ph), yielding the same major diastereomer when using potassium (E)- and (Z)-crotyltrifluoroborate. Its synthetic utility is also illustrated in the total synthesis of (-)-crispine A.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP329976796	Potassium octyltrifluoroborate		329976-79-6	Price

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