Enantio- and Diastereoselective Spiroketalization Catalyzed by Chiral Iridium Complex

Iridium–(P,olefin) complex-catalyzed enantio- and diastereoselective formation of substituted spiroketals from racemic, allylic carbonates is reported, which enables the installation of multiple stereogenic centers in a single operation. The protocol was effective for the preparation of a collection...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 24; pp. 8082 - 8085
Main Authors Hamilton, James Y, Rössler, Simon L, Carreira, Erick M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ENANTIOSELECTIVE ALLYLIC SUBSTITUTION
ASYMMETRIC-SYNTHESIS
ACID
NATURAL-PRODUCTS
ALKYLATION
BIOSYNTHESIS
ALLYLATION
REGIO
SPIROACETALS
DEAROMATIZATION REACTION
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Summary:Iridium–(P,olefin) complex-catalyzed enantio- and diastereoselective formation of substituted spiroketals from racemic, allylic carbonates is reported, which enables the installation of multiple stereogenic centers in a single operation. The protocol was effective for the preparation of a collection of spiroketals of various ring sizes and substituents, including heteroatoms with high enantio- and diastereoselectivity. Furthermore, cascade reactions that couple this enantio- and diastereoselective transformation to additional reversible processes have been achieved to exert concomitant stereocontrol over additional stereogenic centers.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b02856