title: Bimetallic enantioselective approach to axially chiral allenes.
abstract: An efficient bimetallic Zn(II)/Cu(I)-mediated asymmetric synthesis of simple axially chiral allenes from terminal alkynes and aldehydes was realized by taking advantage of the chiral amine (S)-α,α-diphenylprolinol 3. This one-pot procedure is compatible with broad scopes of both terminal alkynes and aldehydes, providing axially chiral allenes in practical yields with an excellent enantioselectivity. Control experiments revealed that CuBr is responsible for the efficient formation of propargylic amine while the combination of CuBr and ZnBr2 plays crucial roles in the amine-to-allene transformation.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, PR China.
authors.forename: Ruizhi
authors.initials: R
authors.lastname: Lü
authors.forename: Juntao
authors.initials: J
authors.lastname: Ye
authors.forename: Tao
authors.initials: T
authors.lastname: Cao
authors.forename: Bo
authors.initials: B
authors.lastname: Chen
authors.forename: Wu
authors.initials: W
authors.lastname: Fan
authors.forename: Weilong
authors.initials: W
authors.lastname: Lin
authors.forename: Jinxian
authors.initials: J
authors.lastname: Liu
authors.forename: Hongwen
authors.initials: H
authors.lastname: Luo
authors.forename: Bukeyan
authors.initials: B
authors.lastname: Miao
authors.forename: Shengjun
authors.initials: S
authors.lastname: Ni
authors.forename: Xinjun
authors.initials: X
authors.lastname: Tang
authors.forename: Nan
authors.initials: N
authors.lastname: Wang
authors.forename: Yuli
authors.initials: Y
authors.lastname: Wang
authors.forename: Xi
authors.initials: X
authors.lastname: Xie
authors.forename: Qiong
authors.initials: Q
authors.lastname: Yu
authors.forename: Weiming
authors.initials: W
authors.lastname: Yuan
authors.forename: Wanli
authors.initials: W
authors.lastname: Zhang
authors.forename: Can
authors.initials: C
authors.lastname: Zhu
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000480:Alkynes; D000588:Amines; D011759:Pyrrolidines; C575987:diphenylprolinol; C025947:propadiene; D003300:Copper; D015032:Zinc