5,5-Dimethyl-2-phenylamino-2-oxazoline as an effective chiral auxiliary for asymmetric alkylations

The novel chiral auxiliaries, 5,5-diphenyl-2-phenylamino-2-oxazoline and 5,5-dimethyl-2-phenylamino-2-oxazoline, were prepared from l-valine methyl ester. The 5,5-dimethyl compound was shown to be a particularly effective chiral auxiliary for asymmetric alkylation affording high yields and diastereo...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 44; pp. 7834 - 7837
Main Authors Le, Thanh Nguyen, Nguyen, Quynh Pham Bao, Kim, Jae Nyoung, Kim, Taek Hyeon
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.10.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
5,5-DIMETHYL-4-ISO-PROPYLOXAZOLIDIN-2-ONE
ALPHA
OXAZOLIDIN-2-ONES
2-PHENYLAMINO-2-OXAZOLINES
ACIDS
DERIVATIVES
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Summary:The novel chiral auxiliaries, 5,5-diphenyl-2-phenylamino-2-oxazoline and 5,5-dimethyl-2-phenylamino-2-oxazoline, were prepared from l-valine methyl ester. The 5,5-dimethyl compound was shown to be a particularly effective chiral auxiliary for asymmetric alkylation affording high yields and diastereoselectivities.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.09.001