Synthesis of novel chiral phosphines from α,α-trehalose

被引：11

作者：

Yonehara, K ^{[1
]}

Hashizume, T ^{[1
]}

Ohe, K ^{[1
]}

Uemura, S ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 20期

关键词：

D O I：

10.1016/S0957-4166(99)00430-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New disaccharide chiral phosphines, such as 4,6-O-benzylidene-2-(diphenylphosphino)-2-deoxy-alpha-D-altropyranosyl-(1,1)-4,6-O-benzylidene-2-(diphenylphosphino)-2-deoxy- alpha-D-altropyranoside 1 and 2-(diphenylphosphino)-2-deoxy-4,6-O-isopropylidene-alpha-D-altropyranosyl-(1, 1)-2-(diphenylphosphino)-2-deoxy-4,6-O-isopropylidene-alpha-D-altropyranoside 9, were prepared from alpha,alpha-treharose. We also succeeded in the synthesis of polyhydroxy chiral diphosphine 2-(diphenylphosphino)-2-deoxy-alpha-D-altropyranosyl-(1,1)-2-(diphenylphosphino)-2-deoxy-alpha-D-altropyranoside 5 by deprotection of isopropylidene groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4029 / 4035

页数：7

共 31 条

[1] PREPARATION OF SOME PARTIALLY PROTECTED, ALPHA,ALPHA-TREHALOSE-TYPE DISACCHARIDES HAVING THE D-ALTRO CONFIGURATION [J].

BAER, HH ;

RADATUS, B .

CARBOHYDRATE RESEARCH, 1984, 128 (01) :165-174

[2] New seven-membered ring chelates with unexpected enantioselectivity induction in asymmetric hydrogenation - Hint for a constant relative enantioselectivity Q for pairs of substrates determined by the structure of the catalysts [J].

Berens, U ;

Selke, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :2055-2064

[3]

Boog-Wick K, 1998, HELV CHIM ACTA, V81, P1622

[4] HYDROFORMYLATION CATALYZED BY RHODIUM COMPLEXES OF TREHALOSE-DERIVED LIGANDS ALPHA-ALPHA-TREDIP AND BETA-BETA-TREDIP - A HIGHLY REGIOSELECTIVE ROUTE TO ALPHA-METHYLARYLPROPIONALDEHYDES [J].

BROWN, JM ;

COOK, SJ .

TETRAHEDRON, 1986, 42 (18) :5105-5109

[5] 2-DIPHENYLARSINO-DERIVATIVE, 2-DIPHENYLPHOSPHINYL-DERIVATIVE, AND 2-TRIPHENYLSTANNYL-DERIVATIVE OF METHYL 4,6-O-BENZYLIDENE-2-DEOXY-ALPHA-D-ALTROPYRANOSIDE - CRYSTAL-STRUCTURE OF THE PHOSPHINYL DERIVATIVE [J].

BROWN, MA ;

COX, PJ ;

HOWIE, RA ;

MELVIN, OA ;

TAYLOR, OJ ;

WARDELL, JL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 498 (02) :275-282

[6] LIGAND ELECTRONIC EFFECTS IN ASYMMETRIC CATALYSIS - ENHANCED ENANTIOSELECTIVITY IN THE ASYMMETRIC HYDROCYANATION OF VINYLARENES [J].

CASALNUOVO, AL ;

RAJANBABU, TV ;

AYERS, TA ;

WARREN, TH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9869-9882

[7]

CULLEN WR, 1978, TETRAHEDRON LETT, P1635

[8]

de Belder A N, 1965, Adv Carbohydr Chem Biochem, V20, P219

[9] SYNTHESIS OF NEW DISUGAR PHOSPHINE-LIGANDS AND THEIR USE IN ASYMMETRIC HYDROGENATION [J].

GILBERTSON, SR ;

CHANG, CWT .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6226-6228

[10] Enantioselective allylic substitution using a novel (phosphino-α-D-glucopyrano-oxazoline)palladium catalyst [J].

Glaser, B ;

Kunz, H .

SYNLETT, 1998, (01) :53-+

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