Diastereoselective Synthesis of Complex cis-Hexahydroindanes by Reductive Alkylation

An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The rea...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 9; pp. 4620 - 4626
Main Authors Kaplan, Hilan Z, Rendina, Victor L, Kingsbury, Jason S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SESQUITERPENES
QUINONE ADDITION-REACTION
CLERODANE DITERPENOIDS
(-)-ILIMAQUINONE
ANALOGS
RADICAL DECARBOXYLATION
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Summary:An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The reaction is convergent, completely diastereoselective, and shows a broad scope with regard to the electrophile.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400670y