Catalytic enantioselective thioester aldol reactions that are compatible with protic functional groups

被引：153

作者：

Magdziak, D ^{[1
]}

Lalic, G ^{[1
]}

Lee, HM ^{[1
]}

Fortner, KC ^{[1
]}

Aloise, AD ^{[1
]}

Shair, MD ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 20期

关键词：

D O I：

10.1021/ja051759j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This communication reports highly enantioselective and diastereoselective methyl malonic acid half thioester (MeMAHT) aldol reactions that are compatible with protic functional groups and enolizable aldehydes, affording syn S-phenyl thiopropionates. Copyright © 2005 American Chemical Society.

引用

页码：7284 / 7285

页数：2

共 23 条

[1] CARREIRA EM, 1999, COMPREHENSIVE ASYMME, V3, P997
[2] Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones
Cortez, GS
Tennyson, RL
Romo, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7945 - 7946
[3] Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates
Evans, DA
Downey, CW
Hubbs, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) : 8706 - 8707
[4] A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction
Evans, DA
Seidel, D
Rueping, M
Lam, HW
Shaw, JT
Downey, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) : 12692 - 12693
[5] C2-symmetric copper(II) complexes as chiral Lewis acids.: Catalytic enantioselective carbonyl-ene reactions with glyoxylate and pyruvate esters
Evans, DA
Tregay, SW
Burgey, CS
Paras, NA
Vojkovsky, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) : 7936 - 7943
[6] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde
Evans, DA
Murry, JA
Kozlowski, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) : 5814 - 5815
[7] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde
Evans, DA
Kozlowski, MC
Murry, JA
Burgey, CS
Campos, KR
Connell, BT
Staples, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 669 - 685
[8] Bis(oxazoline) and bis(oxazolinyl)pyridine copper complexes as enantioselective Diels-Alder catalysts: Reaction scope and synthetic applications
Evans, DA
Barnes, DM
Johnson, JS
Lectka, R
von Matt, P
Miller, SJ
Murry, JA
Norcross, RD
Shaughnessy, EA
Campos, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7582 - 7594
[9] Fukuyama T, 2004, ALDRICHIM ACTA, V37, P87
[10] Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions
Johnson, JS
Evans, DA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 325 - 335

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