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Diastereo- and enantioselective preparation of cyclopropanol derivatives.

ABSTRACT: The diastereoselective carbocupration reaction of alkoxy-functionalized cyclopropene derivatives, followed by a subsequent trapping of the resulting cyclopropylmetal species with an electrophilic source of oxygen (oxenoid) afforded various tetrasubstituted cyclopropanol derivatives in high diastereo- and enantiomeric ratios. Similarly, the enantioselective copper-catalyzed carbomagnesiation/oxidation (or amination) sequence on achiral nonfunctionalized cyclopropenes provided the desired cyclopropanol (and cyclopropylamine) derivatives in excellent diastereo- and enantiomeric excesses.

SUBMITTER: Simaan M

PROVIDER: S-EPMC6444454 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Diastereo- and enantioselective preparation of cyclopropanol derivatives.

Simaan Marwan M Marek Ilan I

Beilstein journal of organic chemistry 20190321

The diastereoselective carbocupration reaction of alkoxy-functionalized cyclopropene derivatives, followed by a subsequent trapping of the resulting cyclopropylmetal species with an electrophilic source of oxygen (oxenoid) afforded various tetrasubstituted cyclopropanol derivatives in high diastereo- and enantiomeric ratios. Similarly, the enantioselective copper-catalyzed carbomagnesiation/oxidation (or amination) sequence on achiral nonfunctionalized cyclopropenes provided the desired cyclopro ...[more]

PMID: 30992723

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