STEREOSELECTIVE SYNTHESIS OF BICYCLIC PYRROLIDINES AND PIPERIDINES VIA THE REDUCTIVE ALKYLATION OF AZIDES WITH ORGANYLDICHLOROBORANES - INTRAMOLECULAR NUCLEOPHILIC-SUBSTITUTION TANDEM SEQUENCE

被引：0

作者：

JEGO, JM ^{[1
]}

CARBONI, B ^{[1
]}

YOUSSOFI, A ^{[1
]}

VAULTIER, M ^{[1
]}

机构：

[1] UNIV RENNES 1,CNRS,URA 704,RECH PHYSICOCHIM STRUCT GRP,AVE GEN LECLERC,F-35042 RENNES,FRANCE

来源：

SYNLETT | 1993年 / 08期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Omega-halogenoalkyldichloroboranes are easily prepared in a stereocontrolled manner by hydroboration of omega-bromoalkylcycloalkenes or Diels-Alder reaction of (E)-alkenyldichloroboranes. Amination with benzylazide followed by an intramolecular nucleophilic substitution afforded the corresponding trans-pyrrolidines or piperidines.

引用

页码：595 / 597

页数：3

共 16 条

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[4] Stereoselective synthesis of bicyclic lactone derivatives via tandem intramolecular Rh(II) catalyzed C-H insertioniring closing metathesis (RCM) sequence.
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[5] A new approach to the synthesis of lactams of muramic, isomuramic and normuramic acids via intramolecular O-alkylation: Stereochemical features of the intramolecular nucleophilic substitution
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[7] New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted γ-lactams:: Synthesis of the tricyclic core of (±)-martinellines
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[8] Synthesis of novel benzopyrano[3,2-c]coumarins via tandem base promoted nucleophilic substitution and intramolecular electrophilic aromatic cyclization
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[9] Enantiospecific synthesis of functionalised bicyclo[3.3.1] nonanes from 10-bromocarvones via tandem intermolecular alkylation-intramolecular Michael addition sequence
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[10] Chiral synthons from carvone .26. Synthesis of chiral bicyclo[3.3.1]nonanes via a tandem intermolecular alkylation-intramolecular Michael reaction sequence
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