Chiral phosphine ligands from amino acids.: II [1] a facile synthesis of phosphinoserines by nucleophilic phosphination reactions -: X-ray structure analyses of Ar2P-CH2CH(NHBOC)(COOMe) (Ar = Ph, m-xylyl)

被引：0

作者：

Brauer, DJ ^{[1
]}

Kottsieper, KW ^{[1
]}

Schenk, S ^{[1
]}

Stelzer, O ^{[1
]}

机构：

[1] Berg Univ Wuppertal, Fachbereich 9, D-42097 Wuppertal, Germany

来源：

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE | 2001年 / 627卷 / 06期

关键词：

phosphorus; phosphinoserines; crystal structures;

D O I：

10.1002/1521-3749(200106)627:6<1151::AID-ZAAC1151>3.0.CO;2-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Phosphino derivatives of serine R2P-CH2-CH(NHBOC)(COOMe) (2a-2d) have been obtained in high yield by nucleophilic phosphination of N-(tert.butoxycarbonyl)-3-iodo-L-alanine methylester with secondary phosphines R2PH (R=Ph, tolyl, 3,5-xylyl, cyclohexyl) in DMF using potassium carbonate as the base. Deprotection of 2b with HCl affords the amino acid ester hydrochloride [2-Tol(2)P-CH2-CH(NH3)(COOMe)]Cl-+(-) (3a). The X-ray structures of 2a (space group P2(1/n)) and 2c (space group P (1) over bar) have been determined. The two enantiomers of 2a or 2c are interconnected by N-H . . .O hydrogen bridges forming dimers in the solid state.

引用

页码：1151 / 1156

页数：6

共 56 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2]

[Anonymous], ANGEW CHEM

[3]

Barret G. C., 1985, Chemistry and Biochemistry of the Amino Acids, DOI 10.1007/978-94-009-4832-7

[4]

Bentrude W. G., 1987, Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, P365

[5] Water-soluble phosphines .6. Tailor-made syntheses of chiral secondary and tertiary phosphines with sulfonated aromatic substituents: Structural and quantum chemical studies [J].

Bitterer, F ;

Herd, O ;

Hessler, A ;

Kuhnel, M ;

Rettig, K ;

Stelzer, O ;

Sheldrick, WS ;

Nagel, S ;

Rosch, N .

INORGANIC CHEMISTRY, 1996, 35 (14) :4103-4113

[6]

BODANCZKY, 1960, CHIMIA, V14, P368

[7] Water soluble phosphines -: Part XIII.: Chiral phosphine ligands with amino acid moieties [J].

Brauer, DJ ;

Schenk, S ;

Rossenbach, S ;

Tepper, M ;

Stelzer, O ;

Häusler, T ;

Sheldrick, WS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 598 (01) :116-126

[8]

BRAUER DJ, IN PRESS EUR J INORG

[9] CRYSTAL + MOLECULAR STRUCTURE OF TRIPHENYL-PHOSPHORUS [J].

DALY, JJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (OCT) :3799-&

[10] TRIPHENYLPHOSPHINE - A REDETERMINATION [J].

DUNNE, BJ ;

ORPEN, AG .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :345-347

← 1 2 3 4 5 6 →