The synthesis of α-amino-γ-substituted adipic acids:: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate

被引：18

作者：

Muller, M ^{[1
]}

Schoenfelder, A ^{[1
]}

Didier, B ^{[1
]}

Mann, A ^{[1
]}

Wermuth, CG ^{[1
]}

机构：

[1] Fac Pharm, Lab Pharmacochim Commun Cellulaire, F-67401 Illkirch, France

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 08期

关键词：

D O I：

10.1039/a809274e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alpha,beta-unsaturated lactam 3 was submitted to 1,4-addition of organocuprate reagents R2CuLiI2 (R = Me, Bu or Ph) to provide the 4-substituted compounds 5a-c, 6a-c as a mixture of diastereomers; these intermediates were then transformed into the corresponding alpha-amino-gamma-substituted adipic acids 7a-c, 8a-c.

引用

页码：683 / 684

页数：2

共 19 条

[1]

ALLINGER NL, 1966, TETRAHEDRON LETT, V7, P1269

[2] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II [J].

BROWN, JD ;

FOLEY, MA ;

COMINS, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7445-7447

[3] Convenient preparations of racemic and enantiopure methyl 6-oxopipecolate [J].

Davies, CE ;

Heightman, TD ;

Hermitage, SA ;

Moloney, MG .

SYNTHETIC COMMUNICATIONS, 1996, 26 (04) :687-696

[4]

Deslongchamps P., 1983, STEREOELECTRONIC EFF, P209

[5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[6] MG2+-LIKE SELECTIVE ANTAGONISM OF EXCITATORY AMINO ACID-INDUCED RESPONSES BY ALPHA-EPSILON-DIAMINOPIMELIC ACID, D-ALPHA-AMINOADIPATE AND HA-966 IN ISOLATED SPINAL-CORD OF FROG AND IMMATURE RAT [J].

EVANS, RH ;

FRANCIS, AA ;

WATKINS, JC .

BRAIN RESEARCH, 1978, 148 (02) :536-542

[7] STEREOSELECTIVE FUNCTIONALIZATION OF N-BOC PYROAMINOADIPIC ACID - SYNTHESIS OF 5-SUBSTITUTED AMINOADIPIC AND PIPECOLIC ACIDS [J].

EZQUERRA, J ;

PEDREGAL, C ;

ESCRIBANO, A ;

CARRENO, MC ;

RUANO, JLG .

TETRAHEDRON LETTERS, 1995, 36 (18) :3247-3250

[8]

GU ZQ, 1995, BIOORG MED CHEM LETT, V5, P1973

[9] A SHORT APPROACH TO FUNCTIONALIZED HOMOCHIRAL PIPERIDINONES [J].

HERMITAGE, SA ;

MOLONEY, MG .

TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1463-1464

[10] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS [J].

HOFFMANN, RW .

CHEMICAL REVIEWS, 1989, 89 (08) :1841-1860

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