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Easy Access to Polyfunctionalized Chiral Decalins.

ABSTRACT: An unexpected ring expansion that converts hydrindanes into decalins via an unprecedented dyotropic reaction involving a mesylate group has been observed, and this paved the way for easy access to polyfunctionalized chiral decalins. These polyfunctionalized chiral decalins can be very useful building blocks for the synthesis of the thia analogues of many natural compounds. They can also be used in asymmetric catalysis and also in the synthesis of the new analogues of vitamin D with a modified D ring and side chain. The use of chiral sulfoxide ligands for asymmetric catalysis or asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds is a very important topic in the field of organic chemistry, hence our results could be useful to the scientific community.

SUBMITTER: Santalla H

PROVIDER: S-EPMC7557988 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Easy Access to Polyfunctionalized Chiral Decalins.

Santalla Hugo H Gándara Zoila Z Gómez-Bouzó Uxía U Gómez Generosa G Fall Yagamare Y

ACS omega 20200929 40

An unexpected ring expansion that converts hydrindanes into decalins via an unprecedented dyotropic reaction involving a mesylate group has been observed, and this paved the way for easy access to polyfunctionalized chiral decalins. These polyfunctionalized chiral decalins can be very useful building blocks for the synthesis of the thia analogues of many natural compounds. They can also be used in asymmetric catalysis and also in the synthesis of the new analogues of vitamin D with a modified D ...[more]

PMID: 33073131

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