Diastereoselective Diels−Alder Reactions of a Novel Cyclopropenyl-Containing Chiral Auxiliary

A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels−Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels−Alder reaction between cy...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 25; pp. 5167 - 5170
Main Authors Henderson, Jeff R, Parvez, Masood, Keay, Brian A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ACID
ACCEPTORS
BUILDING-BLOCKS
REACTIVITY
ALPHA
DERIVATIVES
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Summary:A novel cyclopropenyl-containing 1,3-spiroaminoalcohol auxiliary has been used in a variety of asymmetric Diels−Alder reactions providing endo adducts with diastereomeric ratios ranging from 2:1 up to >99:1. In addition, unexpected regiochemistry was observed for a Diels−Alder reaction between cyclopropenyl dienophile and 4-vinyl-1,2-dihydronapthalene.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702280q