Enantioselective nucleophilic addition of trimethylsilylacetylene to n-phosphinoylimines promoted by C(2)-symmetric proline-derived beta-amino alcohol.
Both C(2)- and C(3)-symmetric proline-derived beta-amine alcohol ligands were designed, synthesized, and successfully applied to the enantioselective direct addition of trimethylsilylacetylene to N-phosphinoylimines. Aromatic, heteroaromatic, and aliphatic N-(diphenylphosphinoyl) imines and several N-(diethoxyphosphoryl) imines were tested, and optically active propargylic amides in good yields (up to 92%) and excellent enantioselectivities (up to 95%) were obtained by the simple experimental procedure. The convenience, mild conditions, and easy deprotection of the phosphonamide products made the present method very attractive. Furthermore, the Michael-type addition process of C horizontal lineN alkynylation was studied and proposed on the basis of React (31)P NMR investigation.
Zhu
Shaoqun
S
Institute of Biochemistry and Molecular Biology and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Yan
Wenjin
W
Mao
Bin
B
Jiang
Xianxing
X
Wang
Rui
R
D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010720:Phosphines / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives*; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000480:Alkynes; D000577:Amides; D000605:Amino Alcohols; D007097:Imines; D010720:Phosphines; D010721:Phosphinic Acids; D020005:Propanols; D014297:Trimethylsilyl Compounds; D011392:Proline; C028255:propargyl alcohol; D000114:Acetylene