Design, Synthesis and Organocatalysis of 2,2′-Biphenol-Based Prolinamide Organocatalysts in the Asymmetric Direct Aldol Reaction in Water

被引：7

作者：

Zhao, Hong-Wu ^{[1
]}

Sheng, Zhi-Hui ^{[1
]}

Meng, Wei ^{[1
]}

Yue, Yuan-Yuan ^{[1
]}

Li, Hai-Long ^{[1
]}

Song, Xiu-Qing ^{[1
]}

Yang, Zhao ^{[1
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

来源：

SYNLETT | 2013年 / 24卷 / 20期

关键词：

axially unfixed 2; 2-biphenol; prolinamide; water-compatible organocatalyst; aldol reaction; stereoselectivity; SMALL ORGANIC-MOLECULES; AQUEOUS-MEDIA; COMPATIBLE ORGANOCATALYSTS; HIGHLY EFFICIENT; CATALYSIS; ALDEHYDES;

D O I：

10.1055/s-0033-1339928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this work, 2,2-biphenol-based prolinamide water-compatible C-2- and C-1-symmetrical organocatalysts were synthesized with the use of enantiopure N-Cbz-(S)-proline as chiral source. Under the optimal reaction conditions, the C-1-symmetrical organocatalyst performed efficiently in the direct aldol reactions in water, thus delivering the desired aldol adducts in high yields (up to 100% yield) with excellent stereocontrol (up to 97:3 dr and 98% ee). The observed stereochemical outcome of the direct aldol reactions in water was interpreted by the proposed transition state.

引用

页码：2743 / 2747

页数：5

共 33 条

[1] Enantioselective organocatalytic aldol reaction using small organic molecules
Bisai, Vishnumaya
Bisai, Alakesh
Singh, Vinod K.
[J]. TETRAHEDRON, 2012, 68 (24) : 4541 - 4580
[2] Direct organocatalytic aldol reactions in buffered aqueous media
Córdova, A
Notz, W
Barbas, CF
[J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
[3] Organocatalytic synthesis of drugs and bioactive natural products
de Figueiredo, Renata Marcia
Christmann, Mathias
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) : 2575 - 2600
[4] Direct Asymmetric Aldol Reactions in Water Catalysed by a Highly Active C2-Symmetrical Bisprolinamide Organocatalyst
Delaney, Joshua P.
Henderson, Luke C.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (01) : 197 - 204
[5] Highly diastereo- and enantioselective direct aldol reactions by 4-tert-butyldimethylsiloxy-substituted organocatalysts derived from N-prolylsulfonamides in water
Fu, Shao-dong
Fu, Xiang-kai
Zhang, Shu-peng
Zou, Xiao-chuan
Wu, Xiao-ju
[J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (20) : 2390 - 2396
[6] Synthesis of reaction-ready 6,6′-biindole and 6,6′-biisatin via palladium(II)-catalysed intramolecular C-H functionalisation
Gamble, Allan B.
Keller, Paul A.
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4076 - 4078
[7] Chitosan Aerogel Beads as a Heterogeneous Organocatalyst for the Asymmetric Aldol Reaction in the Presence of Water: An Assessment of the Effect of Additives
Gioia, Claudio
Ricci, Alfredo
Bernardi, Luca
Bourahla, Khadidja
Tanchoux, Nathalie
Robitzer, Mike
Quignard, Francoise
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (03) : 588 - 594
[8] Highly diastereo- and enantioselective direct aldol reactions in water
Hayashi, Y
Sumiya, T
Takahashi, J
Gotoh, H
Urushima, T
Shoji, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) : 958 - 961
[9] Recent applications of organocatalysts in asymmetric aldol reactions
Heravi, Majid M.
Asadi, Shima
[J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (20-21) : 1431 - 1465
[10] Stereoselective organic reactions in water
Lindström, UM
[J]. CHEMICAL REVIEWS, 2002, 102 (08) : 2751 - 2771

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