Allyl Transfer to Aldehydes and Ketones by Brønsted Acid Activation of Allyl and Crotyl 1,3,2-Dioxazaborolidines

Alkyl dioxazaborolidines are air-stable and often crystalline organoboranes. A variety of Brønsted acids activate allyl dioxazaborolidines to generate reactive allyl-transfer reagents in situ. These reagents add to aldehydes and ketones to generate the corresponding alcohols in good yields under mil...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 21; pp. 4892 - 4895
Main Authors Reilly, Maureen K, Rychnovsky, Scott D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2010
Amer Chemical Soc
Subjects
Acids - chemistry
Aldehydes - chemistry
Allyl Compounds - chemistry
Aza Compounds - chemistry
Chemistry
Chemistry, Organic
Ketones - chemistry
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
CATALYZED CARBONYL ALLYLATION
ASYMMETRIC ALLYLBORATION
ORGANOMETALLIC REAGENTS
LEWIS-ACID
CHIRAL OXAZABOROLIDINE
HOMOALLYLIC ALCOHOLS
ENANTIOSELECTIVE ALLYLATION
CROTYLBORATION
ACETATE
OXIDATION LEVEL
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Summary:Alkyl dioxazaborolidines are air-stable and often crystalline organoboranes. A variety of Brønsted acids activate allyl dioxazaborolidines to generate reactive allyl-transfer reagents in situ. These reagents add to aldehydes and ketones to generate the corresponding alcohols in good yields under mild conditions. The E- and Z-crotyl reagents react diastereoselectively with aldehydes and ketones to produce anti and syn adducts, respectively, a result consistent with a cyclic transition state (type I mechanism).
Bibliography:NIH RePORTER
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1020515