不对称催化最大的工业化例子（20,000 吨/年）， (S)-Metolachlor (Novatis, 1996)

H3COOH3COONCH2ClNCH2ClaR, 1'SaS, 1'S2 active stereoisomers

H3COOH3COONCH2ClNCH2ClaR, 1'RaS, 1'R2 inactive stereoisomers46

HCOHCOO3N[Ir(COD)Cl]2 / L*NHee 79%TON 1 000 000TOF 30 0001'SH3COOH3COONCH2ClNCH2ClaR, 1'SaS, 1'S(S)-Metolachlor萘普生合成（ref. 5）

3ONHClCl1'SPFePPh22Xyl-Josiphos47

COOHMeOH2 / Ru(BINAP)MeOCOOH

97% ee (100% Y)

异喹啉生物碱合成（ref. 6）

NCOMeH2 / Cat*MeOOMeOMe [Rh(R-BINAP)(COD)] ClO4 [Ru(R-BINAP)] (OAc)2

[Ru(R-BINAP)(NEt3)] Cl2

MeO*NCOMeOMeOMe 69% ee 99.5% ee

99% ee

48

香茅醇合成

H2Ru(S-BINAP)

单磷手性配体

OHOHRu(R-BINAP)Ru(S-BINAP)H2OH96 - 99% eeOH49