Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

Diastereoselective Alkylation of 2,3,4,6-Di-O-isopropylidene-2-keto-l-gulonic Amides. Application to the Asymmetric Synthesis of 1-Substituted-1,2,3,4-tetrahydroisoquinolines and 1-Substituted-1,2,3,4,-tetrahydro-β-carbolines

The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonati...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 66; no. 26; pp. 8744 - 8750
Main Authors: Adam, Stéphane, Pannecoucke, Xavier, Combret, Jean-Claude, Quirion, Jean-Charles
Format: Journal Article
Language:English
Published: United States American Chemical Society 28-12-2001
Subjects:
Analytical chemistry
Chemical Sciences
Material chemistry
Organic chemistry
Online Access:Get full text
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Summary:The diastereoselective alkylation of amides 3a,b and 7a,b derived from gulonic acid is described. Substituted compounds are obtained in good yield and high diastereoselectivity. A mechanistic investigation establishes that the diastereoselectivity did not arise from an initial asymmetric deprotonation. The stereochemistry is then determined during the alkylation step.
Bibliography:ark:/67375/TPS-42LMTJ68-N
istex:00B8B13A0DC888BF4ACA979D7E63A4CD4565B378
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0155658