Copper-catalysed enantioconvergent alkylation of oxygen nucleophiles
被引:47
作者:
Chen, Caiyou
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CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Wuhan Univ, Coll Chem & Mol Sci, Wuhan, Peoples R ChinaCALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Chen, Caiyou
[1
,2
]
Fu, Gregory C. C.
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机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USACALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Fu, Gregory C. C.
[1
]
机构:
[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan, Peoples R China
Carbon-oxygen bonds are commonplace in organic molecules, including chiral bioactive compounds; therefore, the development of methods for their construction with simultaneous control of stereoselectivity is an important objective in synthesis. The Williamson ether synthesis, first reported in 1850(1), is the most widely used approach to the alkylation of an oxygen nucleophile, but it has significant limitations (scope and stereochemistry) owing to its reaction mechanism (S(N)2 pathway). Transition-metal catalysis of the coupling of an oxygen nucleophile with an alkyl electrophile has the potential to address these limitations, but progress so far has been limited(2-7), especially with regard to controlling enantioselectivity. Here we establish that a readily available copper catalyst can achieve an array of enantioconvergent substitution reactions of a-haloamides, a useful family of electrophiles, by oxygen nucleophiles; the reaction proceeds under mild conditions in the presence of a wide variety of functional groups. The catalyst is uniquely effective in being able to achieve enantioconvergent alkylations of not only oxygen nucleophiles but also nitrogen nucleophiles, giving support for the potential of transition-metal catalysts to provide a solution to the pivotal challenge of achieving enantioselective alkylations of heteroatom nucleophiles.
机构:
Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Boyer, Cyrille
;
Corrigan, Nathaniel Alan
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Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Corrigan, Nathaniel Alan
;
Jung, Kenward
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Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Jung, Kenward
;
Diep Nguyen
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Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Diep Nguyen
;
Thuy-Khanh Nguyen
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Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Thuy-Khanh Nguyen
;
Adnan, Nik Nik M.
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Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Adnan, Nik Nik M.
;
Oliver, Susan
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Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Oliver, Susan
;
Shanmugam, Sivaprakash
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Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Shanmugam, Sivaprakash
;
Yeow, Jonathan
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Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Ding, Chang-Hua
;
Hou, Xue-Long
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
机构:
Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Boyer, Cyrille
;
Corrigan, Nathaniel Alan
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Corrigan, Nathaniel Alan
;
Jung, Kenward
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Jung, Kenward
;
Diep Nguyen
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Diep Nguyen
;
Thuy-Khanh Nguyen
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机构:
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Thuy-Khanh Nguyen
;
Adnan, Nik Nik M.
论文数: 0引用数: 0
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机构:
Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Adnan, Nik Nik M.
;
Oliver, Susan
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Oliver, Susan
;
Shanmugam, Sivaprakash
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Shanmugam, Sivaprakash
;
Yeow, Jonathan
论文数: 0引用数: 0
h-index: 0
机构:
Univ New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
Univ New S Wales, Sch Chem Engn, CAMD, Sydney, NSW 2052, AustraliaUniv New S Wales, Australian Ctr Nanomed, Sydney, NSW 2052, Australia
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Ding, Chang-Hua
;
Hou, Xue-Long
论文数: 0引用数: 0
h-index: 0
机构:
Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China