A cationic rhodium-chiral diene complex as a high-performance catalyst for the intramolecular asymmetric [4+2] cycloaddition of alkyne-1,3-dienes

被引：68

作者：

Shintani, Ryo ^{[1
]}

Sannohe, Yuta ^{[1
]}

Tsuji, Takaoki ^{[1
]}

Hayashi, Tamio ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 38期

关键词：

asymmetric catalysis; cycloaddition; diene ligands; enantioselectivity; rhodium;

D O I：

10.1002/anie.200702586

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Two rings in one step: A rhodium-diene catalyst is more active than its rhodium-bisphosphine counterpart for the intramolecular [4+2] cycloaddition of alkyne-tethered 1,3-dienes (see scheme). A related complex with a C2-symmetric chiral diene ligand catalyzes an enantioselective asymmetric variant of this process. The intermolecular cycloaddition of 1,3-dienes and alkynes is also highly efficient. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7277 / 7280

页数：4

共 16 条

[11] Synthesis of functionalized tetrahydropyridazines via catalyst-free self [4+2] cycloaddition of in situ generated 1,2-diaza-1,3-dienes
Zhang, Zhimin
Zhang, Li
Chen, Qingqing
Lu, Tao
Zhou, Qingfa
RSC ADVANCES, 2016, 6 (66) : 61680 - 61685
[12] HIGH-PRESSURE (4+2)CYCLOADDITION OF 1-METHOXY-3-TRIALKYLSILYLOXYBUTA-1,3-DIENES TO BUTYL GLYOXYLATE - ISOLATION OF PRIMARY CYCLOADDUCTS
JURCZAK, J
GOLEBIOWSKI, A
RAHM, A
TETRAHEDRON LETTERS, 1986, 27 (07) : 853 - 856
[13] Rhodium-Catalyzed Enantioselective Intramolecular [4+2] Cycloaddition using a Chiral Phosphine-Phosphite Ligand: Importance of Microwave-Assisted Catalyst Conditioning
Falk, Anna
Fiebig, Lukas
Neudoerfl, Joerg-Martin
Adler, Andreas
Schmalz, Hans-Guenther
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) : 3357 - 3362
[14] HIGH-PRESSURE (4+2)CYCLOADDITION OF 1-METHOXYBUTA-1,3-DIENE TO ALPHA-AMINO ALDEHYDES - INFLUENCE OF N-PROTECTING GROUPS ON ASYMMETRIC INDUCTION
JURCZAK, J
GOLEBIOWSKI, A
RACZKO, J
TETRAHEDRON LETTERS, 1988, 29 (46) : 5975 - 5978
[15] ASYMMETRIC INDUCTION IN THE EU(FOD)3-MEDIATED HIGH-PRESSURE (4+2) CYCLOADDITION OF 1-METHOXYBUTA-1,3-DIENE TO 2,3-DI-O-BENZYL-D-GLYCERALDEHYDE
JURCZAK, J
BAUER, T
CARBOHYDRATE RESEARCH, 1987, 160 : C1 - C2
[16] STEREOCHEMISTRY OF DIELS-ALDER REACTION AT HIGH-PRESSURE - INFLUENCE OF PRESSURE ON ASYMMETRIC INDUCTION IN (4+2)CYCLOADDITION OF 1-METHOXYBUTA-1,3-DIENE TO 2,3-0-ISOPROPYLIDENE-D-GLYCERALDEHYDE
JURCZAK, J
BAUER, T
TETRAHEDRON, 1986, 42 (18) : 5045 - 5052

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