Enantioselective cobalt-catalyzed [6+2] cycloadditions of cycloheptatriene with alkynes

被引：44

作者：

Toselli, Nicolas ^{[1
]}

Martin, David ^{[1
]}

Achard, Mathieu ^{[1
]}

Tenaglia, Alphonse ^{[1
]}

Buergi, Thomas ^{[2
]}

Buono, Gerard ^{[1
]}

机构：

[1] Univ Paul Cezanne, CNRS, UMR 6180 Chirotechnol, Lab Synth Asymet, F-13397 Marseille, France

[2] Univ Neuchatel, Inst Chim, CH-2007 Neuchatel, Switzerland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 02期

关键词：

cobalt; cycloaddition reactions; enantioselective catalysis; phosphoramidites; vibrational circular dichroism;

D O I：

10.1002/adsc.200700424

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The enantioselective cobalt-catalyzed [6+ 2] cycloadditions of cycloheptatriene 1 with alkynes 2 is reported. Chiral phosphoramidites based on 3,3'-disubstituted (R)-BINOL appeared to be efficient ligands, affording the corresponding cycloadducts with good yields and up to 92% ee. A vibrational circular dichroism study afforded the absolute configuration of new chiral (+)-(1S,6R)-7-phenyl[4.2.1]bicyclononatriene 3a and (-)-(1S,6R)-7-trimethylsilyl[4.2.1]bicyclononatriene 3c.

引用

页码：280 / 286

页数：7

共 45 条

[41] Chromium(0)-promoted higher-order cycloaddition reactions in organic synthesis
Rigby, JH
[J]. TETRAHEDRON, 1999, 55 (15) : 4521 - 4538
[42] Molybdenum-catalysed and -mediated cycloaddition reactions: Efficient synthesis of complex products from 1-oxa-1,3-dienes and cyclotrienes or -tetraenes
Schmidt, T
[J]. CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (04): : 453 - 461
[43] HIGHLY STEREOSELECTIVE, MOLYBDENUM-CATALYZED [6+2]-CYCLOADDITIONS OF ALPHA,BETA-UNSATURATED KETONES TO CYCLOHEPTA-1,3,5-TRIENE
SCHMIDT, T
BIENEWALD, F
GODDARD, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (16) : 1857 - 1858
[44] TRANSITION-METAL-MEDIATED CYCLO-ADDITION REACTIONS OF ALKYNES IN ORGANIC-SYNTHESIS
SCHORE, NE
[J]. CHEMICAL REVIEWS, 1988, 88 (07) : 1081 - 1119
[45] Transition metal-catalyzed [6+2] cycloadditions of 2-vinylcyclobutanones and alkenes: A new reaction for the synthesis of eight-membered rings
Wender, PA
Correa, AG
Sato, Y
Sun, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) : 7815 - 7816

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