Aziridinium from N,N-dibenzyl serine methyl ester:: Synthesis of enantiomerically pure β-amino and α,β-diamino esters

被引：41

作者：

Couturier, C

Blanchet, A

Schlama, T

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Soc Rhodia, Ctr Rech Lyon, F-69192 St Fons, France

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 10期

关键词：

D O I：

10.1021/ol060700u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of N,N-dibenzyl-O-methylsulfonyl serine methyl ester with a variety of heteronucleophiles (sodium azide, sodium phthalimide, amines, thiols) and carbanions (sodium malonate) gave, via an aziridinium intermediate, the corresponding beta-amino or alpha,beta-diamino ester in good to excellent yield. A short synthesis of orthogonally protected and enantiomerically pure 2,3-diamino propionate (Dap) is described.

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页码：2183 / 2186

页数：4

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共 66 条

[1] Stereodivergent synthesis of all diastereomers of 4-aminoheptane-3,5-diol from (L)-serine [J].

Andrés, JM ;

Pedrosa, R .

TETRAHEDRON, 1998, 54 (21) :5607-5616

[2] NOTE ON THE PREPARATION OF N-SUBSTITUTED AMINOGLYCERALDEHYDES [J].

ANGRICK, M .

MONATSHEFTE FUR CHEMIE, 1985, 116 (05) :645-649

[3] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].

ARNOLD, LD ;

MAY, RG ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241

[4] SYNTHESIS OF (S)-2-AMINO-3-(3-TERT-BUTYL-5-OXO-2H-ISOXAZOL-4-YL)PROPIONIC ACID [J].

ATFANI, M ;

LUBELL, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3184-3188

[5] ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS [J].

BAJGROWICZ, JA ;

ELHALLAOUI, A ;

JACQUIER, R ;

PIGIERE, C ;

VIALLEFONT, P .

TETRAHEDRON, 1985, 41 (10) :1833-1843

[6] CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].

BALDWIN, JE ;

SPIVEY, AC ;

SCHOFIELD, CJ .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884

[7] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ONEIL, IA ;

SCHOFIELD, C ;

SPIVEY, AC ;

SWEENEY, JB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854

[8] Synthesis of cis and trans isomers of an isoxazoline ring-hydroxylated metabolite of Roxifiban, a platelet glycoprotein IIb/IIIa receptor antagonist [J].

Batt, DG ;

Houghton, GC ;

Daneker, WF ;

Jadhav, PK .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :8100-8104

[9] STUDIES ON THE SYNTHESIS AND RESOLUTION OF GAMMA-CARBOXYGLUTAMIC ACID-DERIVATIVES [J].

BOGGS, NT ;

GOLDSMITH, B ;

GAWLEY, RE ;

KOEHLER, KA ;

HISKEY, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2262-2269

[10] Orthogonally protected lanthionines: Synthesis and use for the solid-phase synthesis of an analogue of nisin ring C [J].

Bregant, S ;

Tabor, AB .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2430-2438

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