Enantioselective Synthesis of α-exo-Methylene γ-Butyrolactones via Chromium Catalysis.
Enantioenriched α-exo-methylene γ-butyrolactones have been obtained via a two-step sequence consisting of a highly enantioselective chromium-catalyzed carbonyl 2-(alkoxycarbonyl)allylation and lactonization. A variety of functional groups are compatible under the mild reaction conditions. The synthetic utility of this methodology was demonstrated by two short derivatization transformations and the enantioselective synthesis of (+)-methylenolactocin.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
Weiqiang
W
Chen
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
Qin
Q
Yang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
Tian
T
Zhou
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
Qingshan
Q
Tian
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, P. R. China.
Guozhu
G
Zhang
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002857:Chromium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D007783:Lactones; D009942:Organometallic Compounds; D002857:Chromium; C056801:methylenolactocin; C014096:alpha-methylene gamma-butyrolactone; C011727:chromium hexacarbonyl; D015107:4-Butyrolactone