Cyclizations of acetoxydienes 1 with Pd(PPh(3))(4)/Et(2)Zn (0.05/4-5 mol-equiv.) in Et(2)O at reflux, followed by either protonation, iodination or cyanation, provide cis-disubstituted cyclopentanes and pyrrolidines 5, 7 or 9. These tandem reactions, as well as the conversions 15 --> 17 or 18 and 20 --> 22 show good to excellent regio- and stereocontrol, which is compared to those of Pd-ene ring closures of 1 and 20.
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
Yuan, Zheliang
Peng, Haihui
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
Peng, Haihui
Liu, Guosheng
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Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R ChinaChinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China