We describe a titanocene(III)-catalyzed deuterosilylation of epoxides that provides beta-deuterated anti-Markovnikov alcohols with excellent D-incorporation, in high yield, and often excellent diastereoselectivity after desilylation. The key to the success of the reaction is a novel activation method of Cp2TiCl2 and (tBuC(5)H(4))(2)TiCl2 with BnMgBr and PhSiD3 to provide [(RC5H4)(2)Ti(III)D] without isotope scrambling. It was developed after discovering an off-cycle scrambling with the previously described method. Our precision deuteration can be applied to the synthesis of drug precursors and highlights the power of combining radical chemistry with organometallic catalysis.
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Wu, Xiangyu
Hao, Wei
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Hao, Wei
Ye, Ke-Yin
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Ye, Ke-Yin
Jiang, Binyang
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Jiang, Binyang
Pombar, Gisselle
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Pombar, Gisselle
Song, Zhidong
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h-index: 0
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Song, Zhidong
Lin, Song
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Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
机构:
Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USAColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Yao, Chengbo
Dahmen, Tobias
论文数: 0引用数: 0
h-index: 0
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Dottikon Exclus Synth AG, Hembrunnstr 17, CH-5605 Dottikon, SwitzerlandColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Dahmen, Tobias
Gansaeuer, Andreas
论文数: 0引用数: 0
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Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhard Domagk Str 1, D-53121 Bonn, GermanyColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Gansaeuer, Andreas
Norton, Jack
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Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USAColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
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Univ S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Zesiewicz, Theresa
Heerinckx, Frederic
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Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Heerinckx, Frederic
De Jager, Robert
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Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
De Jager, Robert
Omidvar, Omid
论文数: 0引用数: 0
h-index: 0
机构:
Collaborat Neurosci Network, Long Beach, CA USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Omidvar, Omid
Kilpatrick, Marcus
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Univ S Florida, Coll Educ, Tampa, FL 33620 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Kilpatrick, Marcus
Shaw, Jessica
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h-index: 0
机构:
Univ S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Shaw, Jessica
Shchepinov, Mikhail S.
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h-index: 0
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Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Wu, Xiangyu
Hao, Wei
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Hao, Wei
Ye, Ke-Yin
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Ye, Ke-Yin
Jiang, Binyang
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Jiang, Binyang
Pombar, Gisselle
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Pombar, Gisselle
Song, Zhidong
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
Song, Zhidong
Lin, Song
论文数: 0引用数: 0
h-index: 0
机构:
Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USACornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
机构:
Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USAColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Yao, Chengbo
Dahmen, Tobias
论文数: 0引用数: 0
h-index: 0
机构:
Dottikon Exclus Synth AG, Hembrunnstr 17, CH-5605 Dottikon, SwitzerlandColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Dahmen, Tobias
Gansaeuer, Andreas
论文数: 0引用数: 0
h-index: 0
机构:
Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhard Domagk Str 1, D-53121 Bonn, GermanyColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
Gansaeuer, Andreas
Norton, Jack
论文数: 0引用数: 0
h-index: 0
机构:
Columbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USAColumbia Univ, Dept Chem, 3000 Broadway, New York, NY 10027 USA
机构:
Univ S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Zesiewicz, Theresa
Heerinckx, Frederic
论文数: 0引用数: 0
h-index: 0
机构:
Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Heerinckx, Frederic
De Jager, Robert
论文数: 0引用数: 0
h-index: 0
机构:
Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
De Jager, Robert
Omidvar, Omid
论文数: 0引用数: 0
h-index: 0
机构:
Collaborat Neurosci Network, Long Beach, CA USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Omidvar, Omid
Kilpatrick, Marcus
论文数: 0引用数: 0
h-index: 0
机构:
Univ S Florida, Coll Educ, Tampa, FL 33620 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Kilpatrick, Marcus
Shaw, Jessica
论文数: 0引用数: 0
h-index: 0
机构:
Univ S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA
Shaw, Jessica
Shchepinov, Mikhail S.
论文数: 0引用数: 0
h-index: 0
机构:
Retrotope Inc, 4300 El Camino Real,Suite 201, Los Altos, CA 94022 USAUniv S Florida, Dept Neurol, 12901 Bruce B Downs Blvd,MDC 55, Tampa, FL 33612 USA