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Stereoselective Synthesis of Polysubstituted Spiropentanes.

ABSTRACT: A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp²-disubstituted cyclopropenes. The control of selectivity originates from a combined syn-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with up to five contiguous stereocenters.

SUBMITTER: Cohen Y

PROVIDER: S-EPMC9501800 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Polysubstituted Spiropentanes.

Cohen Yair Y Toledano Dor D Marek Ilan I

Journal of the American Chemical Society 20220911 37

A new approach to polysubstituted spiropentanes is developed through a regio- and diastereoselective carbometalation of sp<sup>2</sup>-disubstituted cyclopropenes. The control of selectivity originates from a combined <i>syn</i>-facial diastereoselective carbometalation with a regio-directed addition. The regio-controlling element subsequently serves as a leaving group in an intramolecular nucleophilic substitution. This method allows the preparation of various polysubstituted spiropentanes with ...[more]

PMID: 36088586

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