Document Detail

Allyl transfer to aldehydes and ketones by Brønsted acid activation of allyl and crotyl 1,3,2-dioxazaborolidines.
MedLine Citation:
PMID:  20942379     Owner:  NLM     Status:  MEDLINE    
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).
Maureen K Reilly; Scott D Rychnovsky
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic letters     Volume:  12     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-10-29     Completed Date:  2011-01-28     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4892-5     Citation Subset:  IM    
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MeSH Terms
Acids / chemistry*
Aldehydes / chemistry*
Allyl Compounds / chemistry*
Aza Compounds / chemistry*
Ketones / chemistry*
Models, Molecular
Molecular Structure
Grant Support
Reg. No./Substance:
0/Acids; 0/Aldehydes; 0/Allyl Compounds; 0/Aza Compounds; 0/Ketones

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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