The enantioselective silver-catalyzed propargylation of N-sulfonylketimines is described. This reaction proceeds in high yield and excellent enantiomeric ratio and is compatible with a wide variety of diaryl-and alkylketimines. Synthetic transformations of homopropargylic products via enyne ring-closing metathesis, Sonogashira cross-coupling, and reduction reactions proceed with high stereochemical fidelity. Both allenyl and propargyl borolane reagents can be used to obtain homopropargylic products, a distribution most consistent with a mechanism involving transmetalation of the silver catalyst with the borolane reagent.
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Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R ChinaChinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
Chen, Diao
Xu, Ming-Hua
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Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R ChinaChinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
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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
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STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
ELSEVIER, CJ
KLEIJN, H
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STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
KLEIJN, H
BOERSMA, J
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STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
BOERSMA, J
VERMEER, P
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STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
机构:
Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R ChinaChinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
Chen, Diao
Xu, Ming-Hua
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机构:
Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R ChinaChinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
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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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
机构:
STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
ELSEVIER, CJ
KLEIJN, H
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机构:
STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
KLEIJN, H
BOERSMA, J
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h-index: 0
机构:
STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS
BOERSMA, J
VERMEER, P
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h-index: 0
机构:
STATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDSSTATE UNIV UTRECHT,DEPT ORGAN CHEM,CROESESTR 79,3522 AD UTRECHT,NETHERLANDS