Organocatalytic highly enantioselective synthesis of secondary α-hydroxyphosphonates

被引：62

作者：

Dodda, Rajasekhar ^{[1
]}

Zhao, Cong-Gui ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol062005s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first organocatalytic cross aldol reaction of ketones and diethyl formylphosphonate hydrate has been realized by using readily available L-prolinamide as the catalyst. Secondary r-hydroxyphosphonates have been synthesized in high enantioselective (up to > 99% ee) and good diastereoselectivity.

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页码：4911 / 4914

页数：4

相关论文

共 49 条

[1] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].

Arai, T ;

Bougauchi, M ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927

[2] Application of fungi as biocatalysts for the reduction of diethyl 1-oxoalkylphosphonates in anhydrous hexane [J].

Brzezinska-Rodak, M ;

Zymanczyk-Duda, E ;

Kafarski, P ;

Lejczak, B .

BIOTECHNOLOGY PROGRESS, 2002, 18 (06) :1287-1291

[3] Synthesis of nonracemic dimethyl α-(hydroxyfarnesyl)phosphonates via oxidation of dimethyl farnesylphosphonate with (camphorsulfonyl)oxaziridines [J].

Cermak, DM ;

Du, YM ;

Wiemer, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :388-393

[4] Theoretical studies of stereoselectivities of intramolecular aldol cyclizations catalyzed by amino acids [J].

Clemente, FR ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11294-11302

[5] NEW INHIBITORS OF RENIN THAT CONTAIN NOVEL PHOSPHOSTATINE LEU-VAL REPLACEMENTS [J].

DELLARIA, JF ;

MAKI, RG ;

STEIN, HH ;

COHEN, J ;

WHITTERN, D ;

MARSH, K ;

HOFFMAN, DJ ;

PLATTNER, JJ ;

PERUN, TJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :534-542

[6]

DRESCHER M, 1995, SYNTHESIS-STUTTGART, P1267

[7] ENZYMES IN ORGANIC-CHEMISTRY .2. LIPASE-CATALYZED HYDROLYSIS OF 1-ACYLOXY-2-ARYLETHYLPHOSPHONATES AND SYNTHESIS OF PHOSPHONIC ACID ANALOGS OF L-PHENYLALANINE AND L-TYROSINE [J].

DRESCHER, M ;

LI, YF ;

HAMMERSCHMIDT, F .

TETRAHEDRON, 1995, 51 (17) :4933-4946

[8] Direct organocatalytic de novo synthesis of carbohydrates [J].

Enders, D ;

Grondal, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (08) :1210-1212

[9] ENANTIOSELECTIVE SYNTHESIS OF DIETHYL 1-HYDROXYALKYLPHOSPHONATES VIA OXAZABOROLIDINE CATALYZED BORANE REDUCTION OF DIETHYL ALPHA-KETOPHOSPHONATES [J].

GAJDA, T .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1965-1972

[10] New homochiral cyclic diol ligands for titanium alkoxide catalyzed phosphonylation of aldehydes [J].

Groaning, MD ;

Rowe, BJ ;

Spilling, CD .

TETRAHEDRON LETTERS, 1998, 39 (31) :5485-5488

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