Asymmetric Copper‐Catalyzed Carbomagnesiation of Cyclopropenes

Asymmetric Copper‐Catalyzed Carbomagnesiation of Cyclopropenes

The highly diastereo‐ and enantioselective formation of polysubstituted cyclopropanes was easily achieved through the asymmetric copper‐catalyzed carbomagnesiation reaction of nonfunctionalized cyclopropene derivatives. The carbometalated species generated in situ readily undergo C−C and C−X bond‐fo...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 56; no. 24; pp. 6783 - 6787
Main Authors: Dian, Longyang, Müller, Daniel S., Marek, Ilan
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 06-06-2017
Edition:International ed. in English
Subjects:
asymmetric catalysis
carbometalation
configurational stability
Copper
cyclopropanes
cyclopropenes
Enantiomers
Organic compounds
cyclopropanes
cyclopropenes
asymmetric catalysis
configurational stability
carbometalation
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Summary:The highly diastereo‐ and enantioselective formation of polysubstituted cyclopropanes was easily achieved through the asymmetric copper‐catalyzed carbomagnesiation reaction of nonfunctionalized cyclopropene derivatives. The carbometalated species generated in situ readily undergo C−C and C−X bond‐forming reactions with various electrophiles with complete retention of configuration. Magnesiated: Diastereo‐ and enantiomerically enriched cyclopropylmagnesium halides were synthesized through the copper‐catalyzed addition of Grignard reagents across cyclopropenes. The carbometalated species generated in situ readily undergo C−C and C−X bond‐forming reactions with various electrophiles with complete retention of configuration.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201701094