STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO CYCLIC N-ACYLIMINIUM IONS

被引：33

作者：

LUDWIG, C ^{[1
]}

WISTRAND, LG ^{[1
]}

机构：

[1] LUND UNIV,CTR CHEM,S-22100 LUND,SWEDEN

来源：

ACTA CHEMICA SCANDINAVICA | 1994年 / 48卷 / 04期

关键词：

D O I：

10.3891/acta.chem.scand.48-0367

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Addition of alkylcopper reagents to the chiral N-acyliminium ion 2a occurs with a high degree of trans selectivity, in contrast with the addition of pi-nucleophiles, where cis selectivity has been observed. A mechanism involving the formation of a pre-complex has been proposed in order to account for this selectivity.

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页码：367 / 371

页数：5

相关论文

共 27 条

[1] ENANTIOSELECTIVE SYNTHESIS OF THE CARBAPENEM RING-SYSTEM FROM (S)-PROLINE [J].

ASADA, S ;

KATO, M ;

ASAI, K ;

INEYAMA, T ;

NISHI, S ;

IZAWA, K ;

SHONO, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) :486-488

[2] SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].

BALIAH, V ;

JEYARAMAN, R ;

CHANDRASEKARAN, L .

CHEMICAL REVIEWS, 1983, 83 (04) :379-423

[3] 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

[4] ENANTIOSELECTIVE SYNTHESIS OF 7 PYRROLIZIDINE DIOLS FROM A SINGLE PRECURSOR [J].

CHAMBERLIN, AR ;

CHUNG, JYL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4425-4431

[5] ADDITION OF ME2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - AN NMR-STUDY OF THE PI-COMPLEX FORMATION [J].

CHRISTENSON, B ;

OLSSON, T ;

ULLENIUS, C .

TETRAHEDRON, 1989, 45 (02) :523-534

[6] THE ADDITION OF ALKYLZINC IODIDES TO 1-(PHENOXYCARBONYL)-2,3-DIHYDROPYRIDINIUM SALTS - A SYNTHESIS OF 2-ALKYL-DELTA-3-PIPERIDINES [J].

COMINS, DL ;

FOLEY, MA .

TETRAHEDRON LETTERS, 1988, 29 (51) :6711-6714

[7] EVIDENCE FOR A REVERSIBLE D,PI-STAR-COMPLEXATION, BETA-CUPRATION SEQUENCE IN THE CONJUGATE ADDITION-REACTION OF GILMAN REAGENTS WITH ALPHA-ENONES, BETA-ENONES [J].

COREY, EJ ;

BOAZ, NW .

TETRAHEDRON LETTERS, 1985, 26 (49) :6015-6018

[8]

HOUSE HO, 1975, J ORG CHEM, V40, P1460, DOI 10.1021/jo00898a019

[9] STEREOSELECTIVE NUCLEOPHILIC-SUBSTITUTION OF 6-METHOXY-1-METHOXYCARBONYLPIPECOLATE - ENANTIOSELECTIVE SYNTHESIS OF (+)-SEDAMINE FROM L-LYSINE [J].

IRIE, K ;

AOE, K ;

TANAKA, T ;

SAITO, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :633-635

[10]

OVERMAN LE, 1989, J ORG CHEM, V54, P2591