Stereoselective formation of trisubstituted (z)-chloroalkenes adjacent to a tertiary carbon stereogenic center by organocuprate-mediated reduction/alkylation |
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Authors: | Tetsuo Narumi Takuya Kobayakawa Haruo Aikawa Shunsuke Seike Hirokazu Tamamura |
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Institution: | Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , 2-3-10 Kandasurugadai, Chiyoda-ku, Tokyo 101-0062, Japan. |
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Abstract: | A robust and efficient method for the synthesis of trisubstituted (Z)-chloroalkenes is described. A one-pot reaction of γ,γ-dichloro-α,β-enoyl sultams involving organocuprate-mediated reduction/asymmetric alkylation affords α-chiral (Z)-chloroalkene derivatives in moderate to high yields with excellent diastereoselectivity, and allylic alkylation of internal allylic gem-dichlorides is also demonstrated. This study provides the first examples of the use of allylic gem-dichlorides adjacent to the chiral center for novel 1,4-asymmetric induction. |
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