Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

被引：69

作者：

Clayden, J ^{[1
]}

Menet, CJ ^{[1
]}

Tchabanenko, K ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON | 2002年 / 58卷 / 23期

关键词：

kainic acid; stereoselective; cyclization; lithium amide; organolithium;

D O I：

10.1016/S0040-4020(02)00379-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4727 / 4733

页数：7

共 49 条

[11] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[12] Synthetic and mechanistic studies of (2R,3S)-3-vinylmalic acid as a mechanism-based inhibitor of 3-isopropylmalate dehydrogenase [J].

Chiba, A ;

Aoyama, T ;

Suzuki, R ;

Eguchi, T ;

Oshima, T ;

Kakinuma, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) :6159-6165

[13]

Clayden J, 2002, ANGEW CHEM INT EDIT, V41, P1049, DOI 10.1002/1521-3773(20020315)41:6<1049::AID-ANIE1049>3.0.CO

[14]

2-7

[15] Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides:: formal synthesis of (-)-kainic acid [J].

Clayden, J ;

Menet, CJ ;

Mansfield, DJ .

CHEMICAL COMMUNICATIONS, 2002, (01) :38-39

[16] Pyrrolidinone-fused cyclohexenones by regioselective dearomatising anionic cyclisation of 2-, 3- or 4-methoxybenzamides [J].

Clayden, J ;

Tchabanenko, K ;

Yasin, SA ;

Turnbull, MD .

SYNLETT, 2001, (02) :302-304

[17] Dearomatizing anionic cyclization of substituted N-cumyl-N-benzylbenzamides on treatment with LDA:: Synthesis of partially saturated substituted isoindolones [J].

Clayden, J ;

Menet, CJ ;

Mansfield, DJ .

ORGANIC LETTERS, 2000, 2 (26) :4229-4232

[18] Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide [J].

Clayden, J ;

Tchabanenko, K .

CHEMICAL COMMUNICATIONS, 2000, (04) :317-318

[19] Stereocontrolled synthesis of 4-substituted (±)-kainic acids [J].

Collado, I ;

Ezquerra, J ;

Mateo, AI ;

Rubio, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1995-2001

[20]

Crudden CM, 2000, ANGEW CHEM INT EDIT, V39, P2851, DOI 10.1002/1521-3773(20000818)39:16<2851::AID-ANIE2851>3.0.CO

← 1 2 3 4 5 →