Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

被引：32

作者：

Bragg, RA ^{[1
]}

Clayden, J ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(99)01765-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as alpha-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8323 / 8326

页数：4

共 19 条

[1] Dearomatising cyclisations of lithiated N-benzylbenzamides [J].

Ahmed, A ;

Clayden, J ;

Yasin, SA .

CHEMICAL COMMUNICATIONS, 1999, (03) :231-232

[2] Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

CHEMICAL COMMUNICATIONS, 1998, (03) :297-298

[3] Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

TETRAHEDRON LETTERS, 1998, 39 (34) :6103-6106

[4] Reaction of organolithiums with fluoro-N,N-diallylanilines: A benzyne-mediated anionic cascade leading to 3,4-disubstituted indolines [J].

Bailey, WF ;

Carson, MW .

TETRAHEDRON LETTERS, 1997, 38 (08) :1329-1332

[5] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[6] REDUCTIVE LITHIATION MEDIATED ANIONIC CYCLIZATIONS AND [2,3]-SIGMATROPIC REARRANGEMENTS [J].

BROKA, CA ;

SHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2981-2984

[7] SYNTHESIS OF DL-PENTALENOLACTONE DL-PENTALENOLACTONE-F [J].

CANE, DE ;

THOMAS, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5295-5303

[8]

CLIFFE IA, 1985, SYNTHESIS-STUTTGART, P1138

[9] Synthesis of 3-alkylpyrrolidines by anionic cyclization [J].

Coldham, I ;

Hufton, R .

TETRAHEDRON, 1996, 52 (38) :12541-12552

[10] Anionic cyclizations of alpha-aminoorganolithiums. Determination of the stereoselectivity at the carbanion center and the synthesis of (+)-pseudoheliotridane [J].

Coldham, I ;

Hufton, R ;

Snowden, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (22) :5322-5323

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