环胺类骨架的联二萘酚配体催化炔烃对N-二苯基膦酰亚胺不对称加成反应研究
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摘要
本文发展了一种新的简便方法,用于制备系列含环胺类骨架的联二萘酚(BINOL-Cycloamine)配体。此类配体联合Et_2Zn,可用于催化端基炔对N-二苯基膦酰亚胺的不对称加成反应,合成炔丙基胺类产物。其中筛选出的配体能有效催化合成炔丙基胺类产物,产率高达85%,对映选择性ee值57%。
A new and convenient method for the preparation of a series of BINOL-Cycloamine ligands had been developed.These ligands in combination with ZnEt_2 were used to catalyze the reaction of N-(diphenylphosphinoyl)imines with terminal alkynes for the asymmetric synthesis of propargylic amines.One of the ligands was found to exhibit good yield(85%)and promising enantioselectivity(57%ee).
A new and convenient method for the preparation of a series of BINOL-Cycloamine ligands had been developed.These ligands in combination with ZnEt_2 were used to catalyze the reaction of N-(diphenylphosphinoyl)imines with terminal alkynes for the asymmetric synthesis of propargylic amines.One of the ligands was found to exhibit good yield(85%)and promising enantioselectivity(57%ee).
引文
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[4]Fleming JJ,Du Bois J.A synthesis of(+)-Saxitoxin[J].J Am Chem Soc,2006,128(12):3 926-3 927.
[5]Moore D,Pu L.BINOL-catalyzed highly enantioselective terminal alkyne additions to aromatic aldehydes[J].Org Lett,2002,4(11):1 855-1 857.
[6]Gao G,Moore D,Xie RG,et al.Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes[J].Org Lett,2002,4(23):4 143-4 146.
[7]Du Y,Turlington M,Zhou X,et al.Highly enantioselective addition of linear alkyl alkynes to linear aldehydes[J].Tetrahedron Lett,2010,51(38):5 024-5 027.
[8]Zhou Y,Wang R,Xu Z,et al.Highly enantioselective phenylacetylene additions to ketones catalyzed by(S)-BINOL-Ti complex[J].Org Lett,2004,6(23):4 147-4 149.
[9]Gao G,Wang Q,Yu XQ,et al.Highly enantioselective synthesis of γ-hydroxy-α,β-acetylenic esters by asymmetric alkyne addition to aldehydes[J].Angew Chem Int Ed,2006,45(1):122-125.
[10]Huang J,Wei S,Wang L,et al.Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes[J].Tetrahedron:Asymmetry,2016,27(9):428-435.
[11]Turlington M,Du Y,Ostrum SG,et al.From highly enantioselective catalytic reaction of 1,3-diynes with aldehydes to facile asymmetric synthesis of polycyclic compounds[J].J Am Chem Soc,2011,133(30):11 780-11 794.
[12]Blay G,Ceballos E,Monleón A,et al.Enantioselective addition of terminal alkynes to N-(diphenylphosphinoyl)imines catalyzed by Zn-BINOL complexes[J].Tetrahedron,2012,68(9):2 128-2 134.
[13]Ying J,Wu XD,Wang D,et al.Catalytic asymmetric addition of alkyl and aryl alkynes to N-(diphenylphosphinoyl)imines[J].J Org Chem,2016,81(19):8 900-8 905.
[14]Hu L,Yu S,Wang Y,et al.Enhanced fluorescence of 3,3′-diformyl BINOL by functional secondary amines[J].Org Lett,2017,19(14):3 779-3 782.
[15]Jennings WB,Lovely CJ.The titanium tetrachloride induced synthesis of N-(diphenylphosphinoyl)imines and N-sulphonylimines directly from aromatic aldehydes[J].Tetrahedron,1991,47(29):5 561-5 568.
[16]Zani L,Alesi S,Cozzi PG,et al.Dimethylzinc-mediated alkynylation of imines[J].J Org Chem,2006,71(4):1 558-1 562.
[17]Cox PJ,Wang W,Snieckus V.Expedient route to 3-and 3,3′-substituted 1,1′-bi-2-naphthols by directed ortho metalation and suzuki cross coupling methods[J].Tetrahedron Lett,1992,33(17):2 253-2 256.