Asymmetric Aldol–Tishchenko Reaction of Sulfinimines

Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol–Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a CN in this type of reaction...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 22; pp. 5642 - 5645
Main Authors Foley, Vera M, McSweeney, Christina M, Eccles, Kevin S, Lawrence, Simon E, McGlacken, Gerard P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
TERT-BUTANESULFINYL IMINES
ACYCLIC AMINO-ALCOHOLS
MANNICH-TYPE REACTION
ENANTIOSELECTIVE SYNTHESIS
BETA-AMINO
ANTI-1,3-AMINO ALCOHOLS
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
1,3-AMINO ALCOHOL DERIVATIVES
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Summary:Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol–Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a CN in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02919