An Asymmetric, Bifunctional Catalytic Approach to Non-Natural α-Amino Acid Derivatives

A catalytic, asymmetric process for the synthesis of 1,4-benzoxazinones from o-benzoquinone imides and ketene enolates is reported. Addition of Lewis acids (Zn(OTf)2, In(OTf)3, and in particular Sc(OTf)3) creates a bifunctional catalytic system that dramatically increases the reaction rate and the y...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2007-07, Vol.72 (14), p.5380-5382
Main Authors: Paull, Daniel H, Alden-Danforth, Ethan, Wolfer, Jamison, Dogo-Isonagie, Cajetan, Abraham, Ciby J, Lectka, Thomas
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Biological Products - chemistry
Catalysis
Catalytic reactions
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Metals - chemistry
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Stereoisomerism
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A catalytic, asymmetric process for the synthesis of 1,4-benzoxazinones from o-benzoquinone imides and ketene enolates is reported. Addition of Lewis acids (Zn(OTf)2, In(OTf)3, and in particular Sc(OTf)3) creates a bifunctional catalytic system that dramatically increases the reaction rate and the yield of these non-natural amino acid precursors while preserving the remarkable enantioselectivity inherent to the reaction. Cocatalyst Sc(OTf)3 increases the yield by up to 42% while producing products in >99% ee.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070472x