55289-73-1Relevant articles and documents
Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
Soltanzadeh, Bardia,Jaganathan, Arvind,Staples, Richard J.,Borhan, Babak
, p. 9517 - 9522 (2015)
An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification. A highly regioselective intermolecular haloetherification that proceeds with excellent enantioselectivity, catalyzed by cinchona alkaloid dimers, is reported. The regioselectivity is preserved for unbiased alkyl substituted allyl amides with either E or Z geometry. (DHQD)2PHAL=hydroquinidine 1,4-phthalazinediyl diether.