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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)158-161
Number of pages4
JournalOrganic Letters
Volume20
Issue number1
DOIs
Publication statusPublished - 2018 Jan 5

Fingerprint

Allylation
potassium
Potassium
synthesis
Amines
amines
catalysts
Catalysts
crispine A

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines : Total Synthesis of (-)-Crispine A. / Chiang, Pei Fen; Li, Wei Sian; Jian, Jia Hong; Kuo, Ting Shen; Wu, Ping Yu; Wu, Hsyueh Liang.

In: Organic Letters, Vol. 20, No. 1, 05.01.2018, p. 158-161.

Research output: Contribution to journalArticle

Chiang, Pei Fen ; Li, Wei Sian ; Jian, Jia Hong ; Kuo, Ting Shen ; Wu, Ping Yu ; Wu, Hsyueh Liang. / Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines : Total Synthesis of (-)-Crispine A. In: Organic Letters. 2018 ; Vol. 20, No. 1. pp. 158-161.
@article{b16b735d8f0b472a9235efa796165350,
title = "Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines: Total Synthesis of (-)-Crispine A",
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.",
author = "Chiang, {Pei Fen} and Li, {Wei Sian} and Jian, {Jia Hong} and Kuo, {Ting Shen} and Wu, {Ping Yu} and Wu, {Hsyueh Liang}",
year = "2018",
month = "1",
day = "5",
doi = "10.1021/acs.orglett.7b03523",
language = "English",
volume = "20",
pages = "158--161",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Rh-Catalyzed Enantioselective Allylation of N-Tosyl- and N-Nosylaldimines

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

PY - 2018/1/5

Y1 - 2018/1/5

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85040245866&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85040245866&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b03523

DO - 10.1021/acs.orglett.7b03523

M3 - Article

AN - SCOPUS:85040245866

VL - 20

SP - 158

EP - 161

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -