Discovery of Annulating Reagents Enabling the One-Step and Highly Stereoselective Synthesis of Cyclopentyl and Cyclohexyl Cores

The use of the unprecedented annulating reagents methyl N-(tert-butylsulfinyl)-4-chlorobutanimidate and methyl N-(tert-butylsulfinyl)-5-bromopentanimidate enables the diastereoselective preparation of 5- and 6-membered carbocycles bearing three contiguous stereocenters. These synthons undergo cycloa...

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Published inOrganic letters Vol. 23; no. 1; pp. 60 - 65
Main Authors McDaniel, Jade, Farley, Christopher A, Ramirez, Antonio, Sandhu, Bhupinder, Sarjeant, Amy, Shi, Qing, Han, Arthur, Gallagher, William P, Hynes, John, Dhar, T. G. Murali, Gonzalez-Bobes, Francisco, Coombs, John R, Marcoux, David
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.01.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
CYCLOPROPANES
RINGS
3+2 CYCLOADDITION
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Summary:The use of the unprecedented annulating reagents methyl N-(tert-butylsulfinyl)-4-chlorobutanimidate and methyl N-(tert-butylsulfinyl)-5-bromopentanimidate enables the diastereoselective preparation of 5- and 6-membered carbocycles bearing three contiguous stereocenters. These synthons undergo cycloaddition with a variety of Michael acceptors to form cyclopentane/cyclohexane rings with excellent stereochemical control, generating only one of the eight possible diastereomers. This novel methodology has enabled the highly enantioselective and high yielding synthesis of novel chemotypes of pharmacological relevance.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03695