Unknown

Dataset Information

0

General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles.


ABSTRACT: Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.

SUBMITTER: Williams DR 

PROVIDER: S-EPMC3566646 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

altmetric image

Publications

General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles.

Williams David R DR   Fu Liangfeng L  

Organic letters 20100201 4


Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles. ...[more]

Similar Datasets

| S-EPMC3454444 | biostudies-literature
| S-EPMC3200820 | biostudies-literature
| S-EPMC7839530 | biostudies-literature
| S-EPMC7325987 | biostudies-literature
| S-EPMC7763531 | biostudies-literature
| S-EPMC3254410 | biostudies-literature
| S-EPMC3588472 | biostudies-literature
| S-EPMC6272547 | biostudies-literature
| S-EPMC8401404 | biostudies-literature
| S-EPMC5727825 | biostudies-literature