Totally Regio- and Stereoselective Behavior of Mono- and Diactivated Cyclic Alkenes in the Lu Reaction: Synthesis of Enantiopure Functionalized Cyclopentanes

被引：36

作者：

Ruano, Jose L. Garcia ^{[1
]}

Nunez, Alberto, Jr. ^{[1
]}

Martin, M. Rosario ^{[1
]}

Fraile, Alberto ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 23期

关键词：

D O I：

10.1021/jo801896a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Alkoxyfuran-2(5H)-ones and their optically pure 3-p-tolylsulfinyl derivatives, synthetic equivalents of the acyclic esters, react with dipoles generated from allenoates and PPh3 (Lu reaction), in a completely regioselective, pi-facial selective and endo-selective manner, yielding bicyclic adducts, which are easily converted into optically pure highly substituted cyclopentane derivatives.

引用

页码：9366 / 9371

页数：6

共 34 条

[1]

Al-Soud YA, 2008, LETT ORG CHEM, V5, P55

[2]

Aversa MC, 2007, CURR ORG CHEM, V11, P1034

[3] ASYMMETRIC DIELS-ALDER REACTIONS OF GAMMA-ALKOXY-ALPHA-SULFINYLBUTENOLIDES [J].

CARRETERO, JC ;

RUANO, JLG ;

LORENTE, A ;

YUSTE, F .

TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :177-180

[4] METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1345-+

[5] 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-+

[6] Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].

Creech, Gardner S. ;

Kwon, Ohyun .

ORGANIC LETTERS, 2008, 10 (03) :429-432

[7] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].

Du, YS ;

Lu, XY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465

[8] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[9] Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes [J].

Dudding, Travis ;

Kwon, Ohyun ;

Mercier, Evan .

ORGANIC LETTERS, 2006, 8 (17) :3643-3646

[10] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

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