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 | |
| Publication status | Published - 2018 Jan 5 |
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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 journal › Article
}
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
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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 -