ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES

被引：44

作者：

AGAMI, C ^{[1
]}

COUTY, F ^{[1
]}

POURSOULIS, M ^{[1
]}

VAISSERMANN, J ^{[1
]}

机构：

[1] UNIV PARIS 06,CHIM METAUX TRANSIT LAB,CNRS,URA 419,F-75230 PARIS 05,FRANCE

来源：

TETRAHEDRON | 1992年 / 48卷 / 03期

关键词：

ENE-IMINIUM CYCLIZATION; HOMOCHIRAL PIPECOLIC ACID DERIVATIVES; GLYOXAL; BETA-AMINO ALCOHOLS;

D O I：

10.1016/S0040-4020(01)89005-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of chiral N-homoallyl beta-amino alcohols with glyoxal produces iminium ions which are cyclized with complete stereoselectivity. These substrates, whose reactivity is closely dependent on the substitution pattern of the ethylenic moiety, undergo ene-iminium cyclizations that ultimately lead to homochiral pipecolic acid derivatives.

引用

页码：431 / 442

页数：12

共 30 条

[1] A NEW CHIRAL GLYCINE-CATION EQUIVALENT - ASYMMETRIC-SYNTHESIS OF OPTICALLY PURE BETA-AMINO ALCOHOLS AND ALPHA-AMINO ESTERS [J].

AGAMI, C ;

COUTY, F ;

DARAN, JC ;

PRINCE, B ;

PUCHOT, C .

TETRAHEDRON LETTERS, 1990, 31 (20) :2889-2892

[2]

AGAMI C, 1990, SYNLETT, P731

[3] DIRECT DERIVATIZATION OF GLYOXAL INTO CHIRAL TEMPLATES PROVIDING COMPLETE DISCRIMINATION BETWEEN THE ALDEHYDE GROUPS [J].

AGAMI, C ;

COUTY, F ;

HAMON, L ;

PRINCE, B ;

PUCHOT, C .

TETRAHEDRON, 1990, 46 (20) :7003-7010

[4] ASYMMETRIC-SYNTHESIS OF N-METHYL-ALPHA-AMINO ESTERS FROM A GLYOXAL DERIVED CHIRAL HETEROCYCLE [J].

AGAMI, C ;

COUTY, F ;

PRINCE, B ;

PUCHOT, C .

TETRAHEDRON, 1991, 47 (25) :4343-4354

[5] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS [J].

ANGLE, SR ;

ARNAIZ, DO .

TETRAHEDRON LETTERS, 1989, 30 (05) :515-518

[6] CHIRAL SYNTHESIS OF 5-HYDROXY-(L)-PIPECOLIC ACIDS FROM (L)-GLUTAMIC ACID [J].

BAILEY, PD ;

BRYANS, JS .

TETRAHEDRON LETTERS, 1988, 29 (18) :2231-2234

[7] ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2S,4S,5S-DIHYDROXYPIPECOLIC ACID, AND BULGECININE FROM DEUTERIUM-GLUCURONOLACTONE [J].

BASHYAL, BP ;

CHOW, HF ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1986, 27 (27) :3205-3208

[8] VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].

BLUMENKOPF, TA ;

OVERMAN, LE .

CHEMICAL REVIEWS, 1986, 86 (05) :857-873

[9]

CALLENS REA, 1982, B SOC CHIM BELG, V91, P713

[10] 4-HYDROXYPIPECOLIC ACID FRM ACACIA SPECIES, AND ITS STEREOISOMERS [J].

CLARKLEWIS, J ;

MORTIMER, PI .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (JAN) :189-&

← 1 2 3 →