Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

被引：43

作者：

Arena, Giada ^{[1
]}

Chen, C. Chun ^{[1
]}

Leonori, Daniele ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

CHIRAL NITRIDOMANGANESE COMPLEX; HIGHLY SUBSTITUTED PYRROLIDINES; CATALYZED CASCADE REACTIONS; EXCITATORY AMINO-ACIDS; ENE-TYPE REACTIONS; ACTIVATED OLEFINS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; KAINIC ACID; (+/-)-ALPHA-ALLOKAINIC ACID;

D O I：

10.1021/ol4020333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

引用

页码：4250 / 4253

页数：4

共 74 条

[31] ASYMMETRIC DIELS-ALDER REACTIONS WITH GAMMA-FUNCTIONALIZED ALPHA,BETA-UNSATURATED CHIRAL N-ACYLOXAZOLIDINONES - SYNTHESIS OF (+)-S-145 [J].

MARTINELLI, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :5065-5073

[32] Pd-catalyzed one-pot coupling of allylamines, activated alkenes, and unsaturated halides (or triflate):: an atom efficient synthesis of highly functionalized pyrrolidines [J].

Martinon, L ;

Azoulay, S ;

Monteiro, N ;

Kündig, EP ;

Balme, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) :3831-3836

[33]

McGeer E. G., 1978, KAINIC ACID AS A TOO

[34] DUPLICATION OF BIOCHEMICAL CHANGES OF HUNTINGTONS-CHOREA BY INTRASTRIATAL INJECTIONS OF GLUTAMIC AND KAINIC ACIDS [J].

MCGEER, EG ;

MCGEER, PL .

NATURE, 1976, 263 (5577) :517-519

[35]

Minakata S, 1998, ANGEW CHEM INT EDIT, V37, P3392, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3392::AID-ANIE3392>3.0.CO

[36]

2-G

[37]

Moloney M. G., 1990, NAT PROD REP, V16, P485

[38] Excitatory amino acids [J].

Moloney, MG .

NATURAL PRODUCT REPORTS, 2002, 19 (05) :597-616

[39]

Moloney MG, 1998, NAT PROD REP, V15, P205

[40] TOTAL SYNTHESIS OF (+/-)-ALPHA-ALLOKAINIC ACID VIA 2 ALLYLSILANE N-ACYLIMINIUM ION REACTIONS [J].

MOOIWEER, HH ;

HIEMSTRA, H ;

SPECKAMP, WN .

TETRAHEDRON, 1991, 47 (20-21) :3451-3462

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