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New isoxazolidine-based chiral auxiliaries for asymmetric syntheses

โœ Scribed by Atsushi Abiko; Ji-Feng Liu; Guo-qiang Wang; Satoru Masamune

Book ID
104256944
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
229 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

New chiral auxiliaries based on the bicyclic-isoxazolidine skeleton, 3-oxa-2,7diazabicylo[3,3,0]octane derivatives, were synthesized in 60-80% overall yields from amino acids. Asymmetric alkylation and boron aldol reaction using the auxiliaries proceeded with high selectivities. "Carboxylic amide" has been used for the asymmetric boron-mediated aldol reaction for the first time.

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: New Isoxazolidine-B
ChemInform Abstract: New Isoxazolidine-Based Chiral Auxiliaries for Asymmetric Syntheses.
โœ A. ABIKO; J.-F. LIU; G. WANG; S. MASAMUNE ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 1 views

New Isoxazolidine-Based Chiral Auxiliaries for Asymmetric Syntheses. -A series of title compounds such as (I) is prepared and tested as auxiliaries. Asymmetric alkylation and boron aldol reactions proceed with excellent selectivity with the derivatives (III) and (VI), respectively. -