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Tethered Silanoxyiodination of Alkenes.

ABSTRACT: We present the first examples of tethered silanoxyiodination reactions of allylic alcohols. The products are useful silanediol organoiodide synthons and are formed with high regioselectivity and diastereocontrol. The reaction is scalable greater than 10-fold without loss of yield or selectivity. Furthermore, the products are starting materials for further transformations, including deiodination, C-N bond installation, epoxide synthesis, and desilylation. DFT calculations provide a basis for understanding the exquisite 6-endo selectivity of this silanoxyiodination reaction and show that the observed products are both kinetically and thermodynamically preferred.

SUBMITTER: Dhokale RA

PROVIDER: S-EPMC9012987 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Tethered Silanoxyiodination of Alkenes.

Dhokale Ranjeet A RA Seidl Frederick J FJ Shinde Anand H AH Mague Joel T JT Sathyamoorthi Shyam S

The Journal of organic chemistry 20210615 13

We present the first examples of tethered silanoxyiodination reactions of allylic alcohols. The products are useful silanediol organoiodide synthons and are formed with high regioselectivity and diastereocontrol. The reaction is scalable greater than 10-fold without loss of yield or selectivity. Furthermore, the products are starting materials for further transformations, including deiodination, C-N bond installation, epoxide synthesis, and desilylation. DFT calculations provide a basis for unde ...[more]

PMID: 34128664

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