Diversity-Oriented Synthesis of Aminocyclohexitols from Garner’s Aldehyde

Ayan Bandyopadhyay; Partha Mitra; Shital K Chattopadhyay

doi:10.1055/s-0032-1317962

Synthesis, Table of Contents

Synthesis 2013; 45(4): 536-544
DOI: 10.1055/s-0032-1317962

paper

Diversity-Oriented Synthesis of Aminocyclohexitols from Garner’s Aldehyde

Ayan Bandyopadhyay

^aDepartment of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India Fax: +91(33)25828282 Email: skchatto@yahoo.com

,

Partha Mitra

^bDivision of X-ray Crystallography, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India

,

Shital K Chattopadhyay*

^aDepartment of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India Fax: +91(33)25828282 Email: skchatto@yahoo.com

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Abstract

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Abstract

A short and efficient synthetic route to three stereoisomeric aminocyclohexane tetrols of the quercitol type has been developed from l-serine, which featured stereoselective allylation, stereocontrolled dihydroxylation, and ring-closing metathesis as key steps.

Key words

allylation - carbocycles - dihydroxylation - metathesis - stereoselective synthesis

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References

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