Asymmetric synthesis of quaternary α-amino phosphonates using sulfinimines

被引：82

作者：

Davis, FA ^{[1
]}

Lee, S ^{[1
]}

Yan, HX ^{[1
]}

Titus, DD ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 11期

关键词：

D O I：

10.1021/ol015945f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of lithium diethylphosphonate to enantiopure ketosulfinimines is highly diastereoselective (> 95%), affording the first examples of quaternary a alkyl ol-amino (arylmethyl)phosphonates.

引用

页码：1757 / 1760

页数：4

共 41 条

[1] PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].

ALLEN, JG ;

ATHERTON, FR ;

HALL, MJ ;

HASSALL, CH ;

HOLMES, SW ;

LAMBERT, RW ;

NISBET, LJ ;

RINGROSE, PS .

NATURE, 1978, 272 (5648) :56-58

[2] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[3]

Alonso E, 2000, SYNLETT, P698

[4] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].

ATHERTON, FR ;

HASSALL, CH ;

LAMBERT, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40

[5] SYNTHESIS OF NOVEL N-PHOSPHONOALKYL DIPEPTIDE INHIBITORS OF HUMAN COLLAGENASE [J].

BIRD, J ;

DEMELLO, RC ;

HARPER, GP ;

HUNTER, DJ ;

KARRAN, EH ;

MARKWELL, RE ;

MILESWILLIAMS, AJ ;

RAHMAN, SS ;

WARD, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (01) :158-169

[6] CONFORMATIONS OF CYCLOHEPTANE [J].

BOCIAN, DF ;

PICKETT, HM ;

ROUNDS, TC ;

STRAUSS, HL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (04) :687-695

[7] Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids [J].

Bravo, P ;

Crucianelli, M ;

Vergani, B ;

Zanda, M .

TETRAHEDRON LETTERS, 1998, 39 (42) :7771-7774

[8] SYNTHESIS OF STEREOCHEMICALLY DEFINED PHOSPHONAMIDATE-CONTAINING PEPTIDES - INHIBITORS FOR THE HIV-1 PROTEINASE [J].

CAMP, NP ;

HAWKINS, PCD ;

HITCHCOCK, PB ;

GANI, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (09) :1047-1052

[9] Stereoselective addition to chiral p-toluene sulfinimines [J].

Chan, WH ;

Lee, AWM ;

Xia, PF ;

Wong, WY .

TETRAHEDRON LETTERS, 2000, 41 (30) :5725-5728

[10] Asymmetric synthesis of 4-hydroxy-3-phenyltetrahydroisoquinolin derivatives using enantiopure sulfinimines (N-sulfinyl imines) [J].

Davis, FA ;

Andemichael, YW .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8627-8634

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