Efficient entry to amino sugars and derivatives via asymmetric organocatalytic Mannich reactions

被引：61

作者：

Enders, Dieter ^{[1
]}

Grondal, Christoph ^{[1
]}

Vrettou, Marianna ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

SYNTHESIS-STUTTGART | 2006年 / 21期

关键词：

organocatalysis; Mannich reaction; amino sugars; asymmetric synthesis; reductive amination;

D O I：

10.1055/S-2006-942542

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient biornimetic C-3+C-n entry to amino sugars and derivatives via a direct asymmetric organocatalytic Mannich methodology employing 2,2-dimethyl-1,3-dioxan-5-one as a dibydroxy-acetone phosphate equivalent and N-PMP or N-Boc protected irnines has been developed. The Mannich bases were obtained in high diastereo- and enantiomeric excesses (78% to > 99% de, 81-98% ee) and were further elaborated using diastereoselective reduction protocols, as well as via diastereoselective direct reductive amination reactions.

引用

页码：3597 / 3604

页数：8

共 55 条

[1]

Arend M., 1998, ANGEW CHEM, V110, P1096, DOI DOI 10.1002/(SICI)1521-3757(19980420)110:8

[2] 2-Nitro thioglycoside donors:: Versatile precursors of β-D-glycosides of aminosugars [J].

Barroca, N ;

Schmidt, RR .

ORGANIC LETTERS, 2004, 6 (10) :1551-1554

[3]

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

[4] Novel and convenient method for the syntheses of 2,6-dideoxypyranoses, 3,6-dideoxypyranoses, and azido (amino) analogs of 3,6-dideoxypyranoses [J].

Chang, CWT ;

Clark, T ;

Ngaara, M .

TETRAHEDRON LETTERS, 2001, 42 (39) :6797-6801

[5] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[6] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

[7] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[8] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[9]

Dalko P.I., 2004, ANGEW CHEM, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[10] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

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