Catalytic Chemo-, Regio-, and Enantioselective Bromochlorination of Allylic Alcohols
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
2015; 137 (11): 3795-3798
Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.
View details for DOI 10.1021/jacs.5b01384
View details for Web of Science ID 000351972000018
View details for PubMedID 25738419
Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
2016; 12: 1361-1365
The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene.
View details for DOI 10.3762/bjoc.12.129
View details for Web of Science ID 000379393800001
View details for PubMedID 27559385
View details for PubMedCentralID PMC4979643