ASYMMETRIC INTRAMOLECULAR ALDOL REACTION MEDIATED BY (S)-N-SUBSTITUTED-N-(2-PYRROLIDINYLMETHYL)AMINE TO PREPARE WIELAND-MIESCHER KETONE

被引：9

作者：

Akahane, Yuichi ^{[1
]}

Inomata, Kohei ^{[1
]}

Endo, Yasuyuki ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

HETEROCYCLES | 2011年 / 82卷 / 02期

关键词：

Organocatalysis; Wieland-Miescher Ketone; N-Substituted-N-(2-pyrrolidinylmethyl)pyrrolidine; Chiral Synthesis; Trifluoroacetic Acid; DIELS-ALDER REACTION; 3,3'-BIMORPHOLINE DERIVATIVES; MICHAEL ADDITION; CHIRAL SYNTHESIS; PROLINE; ORGANOCATALYSIS; DESIGN; CONSTRUCTION; REDUCTION; DIAMINES;

D O I：

10.3987/COM-10-S(E)119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New or known N-substituted-N-(2-pyrrolidinylmethyl)amine derivatives bearing a variety of alkyl and aryl substituents were easily prepared from N-Boc-proline or N'-Boc-N-(2-pyrrolidinylmethyl)amine. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the amine derivative and TFA to prepare Wieland-Miescher ketone was examined. During the examination, optimal amount of TFA in the reaction was identified.

引用

页码：1727 / +

页数：12

共 17 条

[1] A NEW CHIRAL SYNTHESIS OF WIELAND-MIESCHER KETONE CATALYZED BY A COMBINATION OF (S)-N-BENZYL-N-(2-PYRROLIDINYLMETHYL)AMINE DERIVATIVE AND BRONSTED ACID
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HETEROCYCLES, 2009, 77 (02) : 1065 - 1078
[2] ASYMMETRIC INTRAMOLECULAR ALDOL REACTIONS MEDIATED BY CHIRAL TRIAMINES BEARING A PYRROLIDINE SCAFFOLD TO PROVIDE A WIELAND-MIESCHER KETONE
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[8] AN INTRAMOLECULAR NUCLEOPHILE-CATALYZED ALDOL-LACTONIZATION (NCAL) REACTION OF S-ARYL-(E)-6-OXOHEX-2-ENETHIOATE WITH N,N-4-DIMETHYLAMINOPYRIDINE N-OXIDE
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