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Diastereoselective Acyl Nitroso Diels-Alder Reactions Using 1,3-Dienes Derived from (R)-4-tert-Butyldimethylsilyloxy-2-Cyclohexen-1-One
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Diastereoselective Acyl Nitroso Diels-Alder Reactions Using 1,3-Dienes Derived from (R)-4-tert-Butyldimethylsilyloxy-2-Cyclohexen-1-One

Dengfu Lu, Lei Chen, Avishek Roy and Zhendong Jin
SSRN Electronic Journal
Elsevier BV
03/01/2023
DOI: 10.2139/ssrn.4300082
url
https://doi.org/10.1016/j.tetlet.2023.154367View
Published (Version of record)This article has now been published in a journal and has been peer-reviewed by subject experts. This version may differ significantly from the preprint version. Access restricted to faculty, staff and students
url
https://doi.org/10.2139/ssrn.4300082View
Preprint (Author's original)This preprint has not been evaluated by subject experts through peer review. Preprints may undergo extensive changes and/or become peer-reviewed journal articles. Open Access

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Abstract

1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with acyl nitroso dienophiles to form exclusively anti [4+2] cycloaddition products. These regio and diastereoselective acyl nitroso Diels-Alder reactions increase the asymmetric complexity from one chiral center in the starting material to three chiral centers in the products in a single step and provide a powerful approach for the asymmetric synthesis of compounds containing 3,6-dihydro-1,2-oxazine structural feature
 Biochemistry History Organic Chemistry Industrial and Manufacturing Engineering Business and International Management Drug Discovery Polymers and Plastics

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