Synthesis of enantiopure substituted dihydrofurans via the reaction of (S)-glyceraldehyde acetonide- or Garner aldehyde acetonide-derived enones with sulfonium ylides

被引:53
作者
Jiang, YW
Ma, DW
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(02)00239-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of sulfonium ylides with enones derived from 1,3-diketones or ethyl acetoacetate and (S)-glyceraidehyde acetonide or (S)-Garner aldehyde acetonide provides enantiopure polysubstituted dihydrofurans in moderate yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1033 / 1038
页数:6
相关论文
共 8 条
[1]   Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions [J].
Arai, S ;
Nakayama, K ;
Suzuki, Y ;
Hatano, K ;
Shioiri, T .
TETRAHEDRON LETTERS, 1998, 39 (52) :9739-9742
[2]   Scope and diastereoselectivity of the "interrupted" Feist-Benary reaction [J].
Calter, MA ;
Zhu, C .
ORGANIC LETTERS, 2002, 4 (02) :205-208
[3]   Rapid synthesis of the 7-deoxy zaragozic acid core [J].
Calter, MA ;
Zhu, C ;
Lachicotte, RJ .
ORGANIC LETTERS, 2002, 4 (02) :209-212
[4]   One-step palladium-catalyzed synthesis of substituted dihydrofurans from the carbonate derivatives of γ-hydroxy-α,β-unsaturated sulfones [J].
Garrido, JL ;
Alonso, I ;
Carretero, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9406-9413
[5]   Stereocontrolled cyclopropanation of Garner's aldehyde derived enones [J].
Ma, DW ;
Jiang, YW .
TETRAHEDRON-ASYMMETRY, 2000, 11 (18) :3727-3736
[6]   Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins.: Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine [J].
Ma, DW ;
Cao, YY ;
Yang, Y ;
Cheng, DL .
ORGANIC LETTERS, 1999, 1 (02) :285-287
[7]   Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)-glycine via the stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived enones [J].
Ma, DW ;
Cao, YY ;
Wu, WG ;
Jiang, YW .
TETRAHEDRON, 2000, 56 (38) :7447-7456