Asymmetric nitroaldol reaction catalyzed by a C2-symmetric bisoxazolidine ligand

被引：120

作者：

Liu, Shuanglong ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 09期

关键词：

D O I：

10.1021/ol800442s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A C-2-symmetric bisoxazolidine was found to effectively catalyze the asymmetric Henry reaction of aliphatic and aromatic aldehydes. beta-Hydroxy nitroalkanes were produced in up to 99% yield and 95% ee. The bisoxazolidine-catalyzed nitroaldol formation requires relatively short reaction times, proceeds under mild conditions and is applicable to a wide range of substrates including sterically hindered aldehydes.

引用

页码：1831 / 1834

页数：4

共 41 条

[1] Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex [J].

Arai, Takayoshi ;

Watanabe, Masahiko ;

Yanagisawa, Akira .

ORGANIC LETTERS, 2007, 9 (18) :3595-3597

[2] Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes [J].

Bandini, Marco ;

Piccinelli, Fabio ;

Tommasi, Simona ;

Umani-Ronchi, Achille ;

Ventrici, Caterina .

CHEMICAL COMMUNICATIONS, 2007, (06) :616-618

[3] Catalytic asymmetric Henry reaction [J].

Boruwa, Joshodeep ;

Gogoi, Naminita ;

Saikia, Partha Pratim ;

Barua, Nabin C. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3315-3326

[4] Nanocrystalline MgO for asymmetric Henry and Michael reactions [J].

Choudary, BM ;

Ranganath, KVS ;

Pal, U ;

Kantam, ML ;

Sreedhar, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13167-13171

[5] A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].

Evans, DA ;

Seidel, D ;

Rueping, M ;

Lam, HW ;

Shaw, JT ;

Downey, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693

[6] Enantioselective Henry reaction catalyzed by a C2-symmetric bis(oxazoline)-Cu(OAc)2 • H2O complex [J].

Ginotra, Sandeep K. ;

Singh, Vinod K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (24) :3932-3937

[7]

HELMCHEN G, 1995, STEREOSELECTIVE SYNT, V21

[8] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].

KITAMURA, M ;

OKADA, S ;

SUGA, S ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036

[9] Enantioselective Henry reaction catalyzed by salen-cobalt complexes [J].

Kogami, Y ;

Nakajima, T ;

Ikeno, T ;

Yamada, T .

SYNTHESIS-STUTTGART, 2004, (12) :1947-1950

[10] A GENERAL SOLID-PHASE SYNTHESIS STRATEGY FOR THE PREPARATION OF 2-PYRROLIDINEMETHANOL LIGANDS [J].

LIU, GC ;

ELLMAN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7712-7713

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