ChemInform Abstract: Catalytic, Enantioselective Alkylations of N,O-Acetals.

✍ Scribed by Dana Ferraris; Travis Dudding; Brandon Young; William J. Drury III; Thomas Lectka

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199934214

✦ Synopsis

Catalytic, Enantioselective Alkylations of N,O-Acetals.

-The first high-yielding (73-93%) asymmetric alkylations (e.e. up to 96%) of racemic hemiacetals of type (I) with nucleophiles (II) or (V) using a chiral Cu(I)-based catalyst are presented. Several N-protecting sulfonyl groups are tested with a view to their easy removal. The deprotection to yield amine (IV) proceeds with no detectable racemization. A method to synthesize several non-natural amino acids in high yield using readily available precursors via an in situ generation of N,O-acetals is also given. -(FERRARIS, DANA; DUDDING, TRAVIS;