Asymmetric Construction of Spirocyclopentenebenzofuranone Core Structures via Highly Selective Phosphine-Catalyzed [3+2] Cycloaddition Reactions

被引：53

作者：

Albertshofer, Klaus

Tan, Bin

Barbas, Carlos F., III ^{[1
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

BAYLIS-HILLMAN CARBONATES; C2-SYMMETRICAL BIS(PHOSPHOLANES); ENANTIOSELECTIVE CONSTRUCTION; SPIROOXINDOLE DERIVATIVES; ANNULATION; ORGANOCATALYSIS; STEREOCENTERS; EFFICIENT; MICHAEL; IMINES;

D O I：

10.1021/ol401087a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient organocatalytic asymmetric [3 + 2] cycloaddition reaction between 3-substituted methylenebenzofuranone derivatives and diverse Morita-Baylis-Hillman carbonates to provide complex polysubstituted spirocyclopentenebenzofuranone scaffolds In a single step is reported. C2-symmetric phospholanes were efficient nucleophilic catalysts of this transformation under mild conditions, providing reaction products comprised of three consecutive stereocenters, including one all-carbon center, with excellent enantioselectivity.

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页码：2958 / 2961

页数：4

相关论文

共 51 条

[1]

Aladesanmi A. J., 1995, Fitoterapia, V66, P84

[2] Assembly of Spirooxindole Derivatives via Organocatalytic Iminium-Enamine Cascade Reactions [J].

Albertshofer, Klaus ;

Anderson, Kimberly E. ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2012, 14 (23) :5968-5971

[3] Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].

Albertshofer, Klaus ;

Tan, Bin ;

Barbas, Carlos F., III .

ORGANIC LETTERS, 2012, 14 (07) :1834-1837

[4] Organocatalysis - Organocatalysis lost: Modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus [J].

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) :42-47

[5] C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519

[6] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[7] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters [J].

Cao, Yiming ;

Jiang, Xianxing ;

Liu, Luping ;

Shen, Fangfang ;

Zhang, Futing ;

Wang, Rui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9124-9127

[8] Multiple approaches to enantiopure spirocyclic benzofuranones using organocatalytic cascade reactions [J].

Cassani, Carlo ;

Tian, Xu ;

Escudero-Adan, Eduardo C. ;

Melchiorre, Paolo .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :233-235

[9] Asymmetric formation of quaternary carbon centers catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes [J].

Chen, ZG ;

Zhu, GX ;

Jiang, QZ ;

Xiao, DM ;

Cao, P ;

Zhang, X .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5631-5635

[10] Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].

Cowen, Bryan J. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+

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