在膦配位的手性Rh催化劑催化下，前手性烯烴（如雙鍵共軛的羧酸或酰胺）進(jìn)行對映選擇性的氫化的反應(yīng)。
另外除了Rh催化劑，鈦催化的反應(yīng)也有報(bào)道。【Buchwald SL, J Am Chem Soc., 1993, 115, 12569】
反應(yīng)實(shí)例
N-Acetyl-(R)-phenylalanine 2. The rhodium catalyst was obtained by adding (R,R)-DlOP 3 (fromdiethyl tartrarte) to a benzene solution of [RhCl(cyclooctene)2]2 under argon and stirring for 15 min. A solution of the catalyst (1 mmol in EtOH:PhH 4:1) was added under H2 to a solution of
1 (molar ratio catalyst:substrate 1:540). After hydrogenation at 1.1 bar, the solvent was evaporated, the residue was dissolved in 0.5N NaOH and the catalyst was filtered. Acidification and evaporation afforded 2 in 90% yield and 82%ee.
【Kagan HB, J Am Chem Soc., 1972, 94, 6429】
【Buchwald SL, J Am Chem Soc., 1993, 115, 12569】
相關(guān)文獻(xiàn)
1* Horner L Angew Chem Int 1968 7 942
2* Knowles WS J Chem Soc Chem Comm 1968 1445
3* Kagan HB J Chem Soc Chem Comm 1971 481
4* Kagan HB J Am Chem Soc 1972 94 6429
5* Kagan HB J Organomet Chem 1975 90 353
6* Kagan HB Pure Appl Chem 1975 43 401
7* James BR J Organomet Chem 1985 279 31
8* Kagan HB Bull Soc Chim Fr 1988 846
9* Burgess K Tet Asymm 1991 2 613
10* Buchwald SL J Am Chem Soc 1993 115 12569
11* Kagan HB C R Acad Sci Serie Ilb 1996 322 131
12* Zhou QL Tet Asymm 2003 14 3219
13* Jerphagnon T Tet Asymm 2004 15 2101
14* de Bellefon C J Mol Cat A Chem 2007 268 205
編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 246.
