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

[1]

Akahane Y, 2007, HETEROCYCLES, V74, P637

[2] A NEW CHIRAL SYNTHESIS OF WIELAND-MIESCHER KETONE CATALYZED BY A COMBINATION OF (S)-N-BENZYL-N-(2-PYRROLIDINYLMETHYL)AMINE DERIVATIVE AND BRONSTED ACID [J].

Akahane, Yuichi ;

Inomata, Kohei ;

Endo, Yasuyuki .

HETEROCYCLES, 2009, 77 (02) :1065-1078

[3] Towards organocatalytic polyketide synthases with diverse electrophile scope: Trifluoroethyl thioesters as nucleophiles in organocatalytic Michael reactions and beyond [J].

Alonso, Diego A. ;

Kitagaki, Shinji ;

Utsumi, Naoto ;

Barbas, Carlos F., III .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) :4588-4591

[4] ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH CHIRAL HYDRIDE REAGENTS PREPARED FROM LITHIUM ALUMINUM-HYDRIDE AND (S)-2-(N-SUBSTITUTED AMINOMETHYL)PYRROLIDINES [J].

ASAMI, M ;

OHNO, H ;

KOBAYASHI, S ;

MUKAIYAMA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (06) :1869-1873

[5] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[6]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[7] Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids [J].

Bradshaw, Ben ;

Etxebarria-Jardi, Gorka ;

Bonjoch, Josep .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (04) :772-778

[8] Efficient Solvent-Free Robinson Annulation Protocols for the Highly Enantioselective Synthesis of the Wieland-Miescher Ketone and Analogues [J].

Bradshaw, Ben ;

Etxebarria-Jardi, Gorka ;

Bonjoch, Josep ;

Viozquez, Santiago F. ;

Guillena, Gabriela ;

Najera, Carmen .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) :2482-2490

[9] STRUCTURAL STUDIES OF CRYSTALLINE ENAMINES [J].

BROWN, KL ;

HOBI, R ;

DAMM, L ;

DUNITZ, JD ;

ESCHENMOSER, A ;

KRATKY, C .

HELVETICA CHIMICA ACTA, 1978, 61 (08) :3108-3135

[10] L-Proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins [J].

Chen, Halbin ;

Wang, Yu ;

Wei, Siyu ;

Sun, Jian .

TETRAHEDRON-ASYMMETRY, 2007, 18 (11) :1308-1312

← 1 2 3 4 5 →