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Halide Effects on Cyclopropenium Cation Promoted Glycosylation with Deoxy Sugars: Highly α‐Selective Glycosylations Using a 3,3‐Dibromo‐1,2‐diphenylcyclopropene Promoter
Author(s) -
Nogueira Jason M.,
Issa John Paul,
Chu AnHsiang Adam,
Sisel Jordan A.,
Schum Ryan S.,
Bennett Clay S.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200907
Subject(s) - chemistry , glycosylation , glycosyl , sugar , selectivity , glycosyl donor , hemiacetal , combinatorial chemistry , glycoside , halide , organic chemistry , stereochemistry , biochemistry , catalysis
A mixture of 3,3‐dibromocyclopropene and TBAI promotes highly α‐selective glycosylation reactions (up to >20:1) by using deoxy sugar hemiacetal donors. The reaction provides a convenient method for generating highly reactive glycosyl donors in situ from shelf‐stable starting materials. Both armed and disarmed sugars undergo the reaction, and selectivity is independent of the configuration of the donor sugar.