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    
Abstract/OtherAbstract:
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).
Authors:
Maureen K Reilly; Scott D Rychnovsky
Related Documents :
16599619 - Facile n-arylation of amines and sulfonamides and o-arylation of phenols and arenecarbo...
17552569 - Synthesis and reactivity of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole. a novel one-p...
11672269 - Chiral lewis acid-mediated enantioselective pictet-spengler reaction of n(b)-hydroxytry...
20038109 - Cyclobutane amino acid analogues of furanomycin obtained by a formal [2 + 2] cycloaddit...
12201779 - Practical and convenient enzymatic synthesis of enantiopure alpha-amino acids and amides.
21576489 - Isocyanic acid in the atmosphere and its possible link to smoke-related health effects.
9407369 - Ascorbate stimulates type i and type iii collagen in human tenon's fibroblasts.
1712709 - Azelaic acid. a review of its pharmacological properties and therapeutic efficacy in ac...
12953219 - Studies on novel 7-acyl-5-chloro-2-oxo-3h-benzoxazole derivatives as potential analgesi...
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:  2013-07-03    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4892-5     Citation Subset:  IM    
Affiliation:
Department of Chemistry, 1102 Natural Sciences II, University of California-Irvine, Irvine, California 92697, United States.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Acids / chemistry*
Aldehydes / chemistry*
Allyl Compounds / chemistry*
Aza Compounds / chemistry*
Ketones / chemistry*
Models, Molecular
Molecular Structure
Grant Support
ID/Acronym/Agency:
R01 GM043854-19/GM/NIGMS NIH HHS; R01 GM043854-20/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Acids; 0/Aldehydes; 0/Allyl Compounds; 0/Aza Compounds; 0/Ketones
Comments/Corrections

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


Previous Document:  National Hospital Ambulatory Medical Care Survey: 2007 outpatient department summary.
Next Document:  Development of Electrically Conductive Oligo(polyethylene glycol) Fumarate-Polypyrrole Hydrogels for...