Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides
Dong Guk Nam
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Su Yong Shim
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Present address: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
These authors contributed equally to this work.
Search for more papers by this authorHye-Min Jeong
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Search for more papers by this authorCorresponding Author
Dr. Do Hyun Ryu
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Search for more papers by this authorDong Guk Nam
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Su Yong Shim
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Present address: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037 USA
These authors contributed equally to this work.
Search for more papers by this authorHye-Min Jeong
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Search for more papers by this authorCorresponding Author
Dr. Do Hyun Ryu
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-dong, Jangan-gu, Suwon, 16419 Korea
Search for more papers by this authorAbstract
Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.
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