Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides

被引：26

作者：

Sauriat-Dorizon, H ^{[1
]}

Guibé, F ^{[1
]}

机构：

[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab React Organ Select, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

lactam; metathesis; peptide analogues;

D O I：

10.1016/S0040-4039(98)01432-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudopeptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity. (C) 1998 Elsevier Science Lid. All rights reserved.

引用

页码：6711 / 6714

页数：4

共 16 条

[1] IMPROVED STEREOCONTROLLED SYNTHESIS OF THREO PEPTIDYL EPOXIDES
ALBECK, A
PERSKY, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) : 653 - 657
[2] Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[3] AN ENANTIOSELECTIVE AND HIGHLY CONVERGENT SYNTHESIS OF (+)-IKARUGAMYCIN
BOECKMAN, RK
WEIDNER, CH
PERNI, RB
NAPIER, JJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8036 - 8037
[4] GARROHELION F, 1996, J CHEM SOC CHEM COMM, P641
[5] Recent advances in olefin metathesis and its application in organic synthesis
Grubbs, RH
Chang, S
[J]. TETRAHEDRON, 1998, 54 (18) : 4413 - 4450
[6] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS
GRUBBS, RH
MILLER, SJ
FU, GC
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) : 446 - 452
[7] A thermodynamic preference of chiral N-methanesulfonyl and N-arenesulfonyl 2,3-cis-3-alkyl-2-vinylaziridines over their 2,3-trans-isomers: Useful palladium(0)-catalyzed equilibration reactions for the synthesis of (E)-alkene dipeptide isosteres
Ibuka, T
Mimura, N
Aoyama, H
Akaji, M
Ohno, H
Miwa, Y
Taga, T
Nakai, K
Tamamura, H
Fujii, N
Yamamoto, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 999 - 1015
[8] A REVERSIBLE PROTECTING GROUP FOR THE AMIDE BOND IN PEPTIDES - USE IN THE SYNTHESIS OF DIFFICULT SEQUENCES
JOHNSON, T
QUIBELL, M
OWEN, D
SHEPPARD, RC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) : 369 - 372
[9] Asymmetric C-N bond constructions via crotylsilane addition reactions: A stereocontrolled route to dipeptide isosteres
Masse, CE
Knight, BS
Stavropoulos, P
Panek, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) : 6040 - 6047
[10] ASYMMETRIC ALKYLATION OF NORMAL-ACYLSULTAMS - A GENERAL-ROUTE TO ENANTIOMERICALLY PURE, CRYSTALLINE C(ALPHA,ALPHA)-DISUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
OPPOLZER, W
MORETTI, R
THOMI, S
[J]. TETRAHEDRON LETTERS, 1989, 30 (41) : 5603 - 5606

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