SYNTHESIS OF 2,2′-BIS(DIPHENYLPHOSPHINO)-1,1′-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF α-(ACYLAMINO)ACRYLIC ACIDS
SYNTHESIS OF 2,2′-BIS(DIPHENYLPHOSPHINO)-1,1′-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF α-(ACYLAMINO)ACRYLIC ACIDS
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DOI：
10.1002/chin.198113343
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发表时间：
1981
期刊：
影响因子：
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通讯作者：
A. Miyashita;A. Yasuda;H. Takaya;K. Toriumi;Tasuku Ito;T. Souchi;R. Noyori
中科院分区：
文献类型：
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作者：
A. Miyashita;A. Yasuda;H. Takaya;K. Toriumi;Tasuku Ito;T. Souchi;R. Noyori
反应通常用在20-30 mL乙醇（或对于构型不稳定的E底物为THF）中的0.5-1.0 mmol底物在室温下在3-4 atm的初始氢气压力下进行48 h。B根据光学纯化合物的下列值计算光学产率：γ-苯甲酰基-（R）-苯丙氨酸，[M]+ 41.8（c 1，CH3OH）（真实样品，制备）; N-苯甲酰基-N-苯甲酰基-（S）苯丙氨酸甲酯，[a] q-45.3（Cl，C2 H3 OH）（Sinou，D.;卡根，B。J. Organomet. 1976，114，325）; A-乙酰基-（R）苯丙氨酸，[u] q-42.1（cl，CH 3OH）（真实样品，制备的）; Ar-苯甲酰基-3-（4-羟基-3-甲氧基苯基）-（S）-丙氨酸，[a] q-28.5（cl，CH 3OH）（Knowles，W.美国，私人通信）; A-苯甲酰基-（S）-丙氨酸，[a]+26.7（c 1，0.1 N NaOH）（真实样品，制备）。c氢化在THF中进行。
0 The reaction was generally run with 0.5-1.0 mmol of substrate in 20-30 mL ethanol (or THF for configurationally labile Esubstrates) at room temperature for 48 h under an initial hydrogen pressure of 3-4 atm. b Optical yields were calculated with respect to the following val-ues of the optically pure compounds: yV-benzoyl-(R)-phenylalanine,[] ß+ 41.8 (c 1, CH3OH)(authentic sample, prepared);/V-benzoyl-(S> phenylalanine,[u] q-41.4 (c 1, CH3OH)(authentic sample, prepared); vV-benzoyl-(S> phenylalanine methyl ester,[a] q-45.3 (c 1, C2HsOH)(Sinou, D.; Kagan,. B. J. Organomet. Chem. 1976, 114, 325); A-acetyl-(R> phenylalanine,[u] q-42.1 (c 1, CH3OH)(authentic sample, prepared); Ar-benzoyl-3-(4-hydroxy-3-methoxyphenyl)-(S)-alanine,[a]}^-28.5 (c 1, CH3OH)(Knowles, W. S., private communica-tion); A-benzoyl-(S)-alanine,[a]+ 26.7 (c 1, 0.1 N NaOH)(authentic sample, prepared). c Hydrogenation was carried out in THF.