Journal
ORGANIC LETTERS
Volume 18, Issue 23, Pages 6160-6163Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03168
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Funding
- SERB [SB/S1/OC-63/2013]
- CSIR [02(0207)/14/ENIR-II]
- DAE-BRNS [2013/37C/56/BRNS/2440]
- Council of Scientific and Industrial Research (CSIR), New Delhi
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The enantioselective Diels Alder (DA) reaction with monosubstituted p-benzoquinones is an unmet challenge. A new approach for the enantioselective synthesis of monosubstituted quinone-DA adducts is presented based on C(sp(2)) H alkylative desymmetrization of meso-DA adducts. Catalyzed by a tertiary amino-thiourea derivative, this reaction utilizes nitroalkanes as the alkylating agents and generates densely functionalized products bearing at least four contiguous stereogenic centers remote from the reaction site with excellent enantioselectivities.
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