Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes

被引:73
作者
Nelson, SG [1 ]
Zhu, C [1 ]
Shen, XQ [1 ]
机构
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
关键词
D O I
10.1021/ja0391208
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted β-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal′s dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions. Copyright © 2004 American Chemical Society.
引用
收藏
页码:14 / 15
页数:2
相关论文
共 21 条
[1]   First total synthesis of a natural product containing a chiral, β-diketone:: Synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone [J].
Calter, MA ;
Liao, WS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13127-13129
[2]   Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones [J].
Cortez, GS ;
Tennyson, RL ;
Romo, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7945-7946
[3]   Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones [J].
Evans, DA ;
Tedrow, JS ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :392-393
[4]   C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes [J].
Evans, DA ;
Janey, JM .
ORGANIC LETTERS, 2001, 3 (13) :2125-2128
[5]   Catalytic asymmetric homo-aldol reaction of pyruvate - a chiral Lewis acid catalyst that mimics aldolase enzymes [J].
Juhl, K ;
Gathergood, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2000, (22) :2211-2212
[6]   Lewis acidity expressed in neutral electron-rich aluminum(III) complexes: An example of ligand-defined catalysis [J].
Nelson, SG ;
Kim, BK ;
Peelen, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9318-9319
[7]   SN2 ring opening of β-lactones:: An alternative to catalytic asymmetric conjugate additions [J].
Nelson, SG ;
Wan, ZH ;
Stan, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4680-4683
[8]  
Nelson SG, 2000, ANGEW CHEM INT EDIT, V39, P1323, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1323::AID-ANIE1323>3.0.CO
[9]  
2-X
[10]   Mechanistic alternatives in Lewis acid-catalyzed acyl halide-aldehyde cyclocondensations [J].
Nelson, SG ;
Peelen, TJ ;
Wan, ZH .
TETRAHEDRON LETTERS, 1999, 40 (36) :6541-6543