Synthesis of chiral amino allenes via an organocyanocuprate-mediated ring-opening reaction of enantiopure ethynylaziridines

被引：37

作者：

Ohno, H ^{[1
]}

Toda, A ^{[1
]}

Miwa, Y ^{[1
]}

Taga, T ^{[1
]}

Fujii, N ^{[1
]}

Ibuka, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(98)02348-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amino allenes have been synthesized from 2-ethynylaziridines via organocopper-mediated reactions. Whereas treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-2-ethynylaziridines with RCu(CN)M (M = Li or MgX) yield exclusively (S,S)-allenylamines in high yields, isomeric (2S,3S)-2,3-cis-3-alkyl-2-ethynylaziridines afford (S,R)-allenylamines in comparable high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：349 / 352

页数：4

共 51 条

[1] Palladium-catalyzed hydrocarboxylation of allenes
Al-Masum, M
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) : 3809 - 3810
[2] DIASTEREOSELECTIVE SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS FROM PROPARGYLIC EPOXIDES
ALEXAKIS, A
MAREK, I
MANGENEY, P
NORMANT, JF
[J]. TETRAHEDRON LETTERS, 1989, 30 (18) : 2387 - 2390
[3] The two component palladium catalyst system for intermolecular hydroamination of allenes
AlMasum, M
Meguro, M
Yamamoto, Y
[J]. TETRAHEDRON LETTERS, 1997, 38 (34) : 6071 - 6074
[4] Regio- and stereoselectivity in reactions of 2,3-cis- and trans-3-alkyl-2-vinylaziridines with organocopper reagents: Importance of 2,3-cis-stereochemistry in controlling selectivity
Aoyama, H
Mimura, N
Ohno, H
Ishii, K
Toda, A
Tamamura, H
Otaka, A
Fujii, N
Ibuka, T
[J]. TETRAHEDRON LETTERS, 1997, 38 (42) : 7383 - 7386
[5] Organolanthanide-catalyzed intramolecular hydroamination/cyclization of aminoallenes
Arredondo, VM
McDonald, FE
Marks, TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) : 4871 - 4872
[6] CYCLIZATION OF GAMMA-ALLENIC AND DELTA-ALLENIC AMINES - SYNTHESIS OF 2-ALCENYL PYRROLIDINES AND 2-ALCENYL PIPERIDENES
ARSENIYADIS, S
GORE, J
[J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 3997 - 4000
[7] It's on lithium! An answer to the recent communication which asked the question: 'If the cyano ligand is not on copper, then where is it?'
Bertz, SH
Miao, GB
Eriksson, M
[J]. CHEMICAL COMMUNICATIONS, 1996, (07) : 815 - 816
[8] SYNTHESIS OF ALLYLIC AMINES THROUGH THE PALLADIUM-CATALYZED HYDROAMINATION OF ALLENES
BESSON, L
GORE, J
GAZES, B
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3857 - 3860
[9] Boche G, 1998, ANGEW CHEM INT EDIT, V37, P1684, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1684::AID-ANIE1684>3.0.CO
[10] 2-2

← 1 2 3 4 5 6 →