Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficient route to alpha-chiral BCPs, via highly diastereoselective asymmetric enolate functionalization. We also describe the application of this chemistry to the synthesis of BCP analogues of phenylglycine and tarenflurbil, the single enantiomer of the NSAID flurbiprofen.
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
Matsunaga, Tadafumi
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Kanazawa, Junichiro
Ichikawa, Tomohiro
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
Ichikawa, Tomohiro
Harada, Mei
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
Harada, Mei
Nishiyama, Yusuke
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RIKEN, RIKEN JEOL Collaborat Ctr, Tsurumi Ku, Yokohama, Kanagawa 2300045, Japan
RIKEN, SPring Ctr 8, Tsurumi Ku, Yokohama, Kanagawa 2300045, Japan
JEOL RESONANCE Inc, 3-1-2 Musashino, Akishima, Tokyo 1968558, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
Nishiyama, Yusuke
Duong, Nghia Tuan
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RIKEN, RIKEN JEOL Collaborat Ctr, Tsurumi Ku, Yokohama, Kanagawa 2300045, Japan
RIKEN, SPring Ctr 8, Tsurumi Ku, Yokohama, Kanagawa 2300045, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
Duong, Nghia Tuan
Matsumoto, Takashi
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Rigaku Corp, 3-9-12 Matsubara Cho, Akishima, Tokyo 1968666, JapanUniv Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
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UT SouthWestern Med Ctr, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USAUT SouthWestern Med Ctr, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USA
Lu, Yong
Chen, Chuo
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UT SouthWestern Med Ctr, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USAUT SouthWestern Med Ctr, Dept Biochem, 5323 Harry Hines Blvd, Dallas, TX 75390 USA
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Zhu, Ziyue
Tang, Jiaqi
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Tang, Jiaqi
Coe, Matthew
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Coe, Matthew
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Knieb, Alexander
Xu, Yijie
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Xu, Yijie
Lin, Daniel
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Lin, Daniel
Zhang, Chao
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Zhang, Chao
Prakash, G. K. Surya
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Univ Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Dept Chem, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA
Univ Southern Calif, Mork Family Dept Chem Engn & Mat Sci, 837 Bloom Walk 1661, Los Angeles, CA 90089 USAUniv Southern Calif, Loker Hydrocarbon Res Inst, 837 Bloom Walk 1661, Los Angeles, CA 90089 USA