Highly diastereoselective generation of various 3,3-disubstituted allyl boronates for the stereospecific construction of quaternary centers

[Display omitted] Single isomer trisubstituted olefins were converted into allyl boron nucleophiles that were condensed with aldehydes to give products containing quaternary centers. The products were obtained in extremely high diastereomeric ratios, a reflection of the stereochemical integrity of t...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 44; pp. 6085 - 6087
Main Authors Biggs, Robyn Aryn, Lambadaris, Maria, Ogilvie, William W.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.10.2014
Elsevier
Subjects
Boron
Chemistry
Chemistry, Organic
Condensing
Diastereoselective
Integrity
Isomers
Nucleophiles
Olefins
Physical Sciences
Quaternary carbon
Reflection
Science & Technology
Stereochemistry
Tetrahedrons
Trisubstituted olefins
Diastereoselective
Quaternary carbon
Stereochemistry
Trisubstituted olefins
ISOMER TRISUBSTITUTED OLEFINS
TRICHLOROSILANES
CATALYZED ENANTIOSELECTIVE ADDITION
CARBON
LEWIS-ACID
ALLYLBORATION
HOMOALLYLIC ALCOHOLS
ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
STEREOCONTROLLED SYNTHESIS
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Summary:[Display omitted] Single isomer trisubstituted olefins were converted into allyl boron nucleophiles that were condensed with aldehydes to give products containing quaternary centers. The products were obtained in extremely high diastereomeric ratios, a reflection of the stereochemical integrity of the starting materials.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.09.038