Highly concentrated catalytic asymmetric allylation of ketones
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作者:
Wooten, Alfred J.
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Wooten, Alfred J.
[1
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Kim, Jeung Gon
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Kim, Jeung Gon
[1
]
Walsh, Patrick J.
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Walsh, Patrick J.
[1
]
机构:
[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
We report the catalytic asymmetric allylation of ketones under highly concentrated reaction conditions with a catalyst generated from titanium tetraisopropoxide and BINOL (1:2 ratio) in the presence of isopropanol. This catalyst promotes the addition of tetraallylstannane to a variety of ketones to produce tertiary homoallylic alcohols in excellent yield (80-99%) with high enantioselectivities (79-95%). The resulting homoallylic alcohols can also be epoxidized in situ using tert-butyl hydroperoxide (TBHP) to afford cyclic epoxy alcohols in high yield (84-87%).
机构:
Univ Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USA
Waltz, KM
Gavenonis, J
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Univ Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USA
Gavenonis, J
Walsh, PJ
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Univ Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diane T Vagelos Labs, Philadelphia, PA 19104 USA
机构:
Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Kim, JG
Waltz, KM
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Waltz, KM
Garcia, IF
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Garcia, IF
Kwiatkowski, D
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
Kwiatkowski, D
Walsh, PJ
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Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USAUniv Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
机构:Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R China
Liu, Jie
Cao, Chao-Guo
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机构:Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R China
Cao, Chao-Guo
Sun, Hong-Bao
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机构:Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R China
Sun, Hong-Bao
Zhang, Xia
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机构:Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R China
Zhang, Xia
Niu, Dawen
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Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R ChinaSichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Peoples R China