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 46 条

[41] Development of a scalable synthesis of a common eastern tricyclic lactone for construction of the nodulisporic acids [J].

Smith, Amos B., III ;

Kurti, Laszlo ;

Davulcu, Akin H. ;

Cho, Young Shin .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :19-24

[42] Synthesis and use of 3,3′-bimorpholine derivatives in asymmetric Michael addition and intramolecular aldol reaction [J].

Sulzer-Mosse, Sarah ;

Laars, Marju ;

Kriis, Kadri ;

Kanger, Tonis ;

Alexakis, Alexandre .

SYNTHESIS-STUTTGART, 2007, (11) :1729-1732

[43] Direct enantioselective synthesis of bicyclic Diels-Alder products [J].

Sunden, Henrik ;

Rios, Ramon ;

Xu, Yongmei ;

Eriksson, Lars ;

Cordova, Armando .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2549-2555

[44] BASE-CATALYZED REARRANGEMENT OF OXY-COPE SYSTEMS [J].

UMA, R ;

SWAMINATHAN, S ;

RAJAGOPALAN, K .

TETRAHEDRON LETTERS, 1984, 25 (50) :5825-5828

[45] UBER DIE HERSTELLUNG MEHRKERNIGER KETONE [J].

WIELAND, P ;

MIESCHER, K .

HELVETICA CHIMICA ACTA, 1950, 33 (07) :2215-2228

[46] Antibody-catalyzed enantioselective Robinson annulation [J].

Zhong, GF ;

Hoffmann, T ;

Lerner, RA ;

Danishefsky, S ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8131-8132

← 1 2 3 4 5 →