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

doi:10.1021/acs.orglett.7b03523

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

Department of Chemistry

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5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	158-161
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.7b03523
Publication status	Published - 2018 Jan 5

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ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Chiang, P. F., Li, W. S., Jian, J. H., Kuo, T. S., Wu, P. Y., & Wu, H. L. (2018). Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A. Organic Letters, 20(1), 158-161. https://doi.org/10.1021/acs.orglett.7b03523

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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.",

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T2 - Total Synthesis of (-)-Crispine A

AU - Chiang, Pei Fen

AU - Li, Wei Sian

AU - Jian, Jia Hong

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

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AB - 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.

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10.1021/acs.orglett.7b03523