Asymmetric Mukaiyama aldol coupling between anti α-methyl-β-hydroxy enol silanes and propanal catalyzed by chiral binaphthol-titanium complex

Tetrahedron Letters

Volumn 40, Issue 6, 1999, Pages 1121-1122

  Delas, Christophe ^a   Szymoniak, Jan ^b   Lefranc, Hervé ^a   Moïse, Claude ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYL BETA HYDROXY ENOL SILANE; KETOL; PROPIONALDEHYDE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; PROMOTER REGION; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0033524754     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02583-0     Document Type: Article

References (11)

1. [1] Szymoniak, J.; Lefranc, H. ; Moïse, C., J. Org. Chem. 1996; 61: 3926-3928;
2. for the synthetic uses of allylmetals (allyltitanocenes) see : Yamamoto, Y., Asao, N., Chem. Rev. 1993; 93: 2207-2293; Sato, F.; Iijima, S.; Sato, M., Tetrahedron Lett. 1981; 22 : 243-246; Sato, F.; Uchiyama, H.; Iida, K.; Kobayashi, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1983 : 921-922.
3. for the synthetic uses of allylmetals (allyltitanocenes)see : Yamamoto, Y., Asao, N., Chem. Rev. 1993; 93: 2207-2293; Sato, F.; Iijima, S.; Sato, M., Tetrahedron Lett. 1981; 22 : 243-246; Sato, F.; Uchiyama, H.; Iida, K.; Kobayashi, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1983 : 921-922.
4. for the synthetic uses of allylmetals (allyltitanocenes)see : Yamamoto, Y., Asao, N., Chem. Rev. 1993; 93: 2207-2293; Sato, F.; Iijima, S.; Sato, M., Tetrahedron Lett. 1981; 22 : 243-246; Sato, F.; Uchiyama, H.; Iida, K.; Kobayashi, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1983 : 921-922.
5. [2] Hoffmann, R.W. Stereocontrolled Organic Synthesis ; Trost, B.M., ed. ; Blackwell Scientific Publications : Oxford, 1994 : p.259.
6. [3] Lefranc, H. ; Szymoniak, J. ; Tréma, R. ;Moïse, C., Synth. Commun. 1997 ; 27: 1689-1695.
7. [4] This derivative has been succesfully used to catalyze [4+2] cycloadditions, ene reactions, additions of allylmetals to the carbonyl compounds, and some Mukaiyama reactions ; Mikami, K.; Motoyama, Y.; Terada, M., J. Am. Chem. Soc. 1994; 116: 2812-2820;
8. Mikami, K; Terada, M.; Nakai, T., J. Am. Chem. Soc. 1990; 112 : 3949-3954; Mukaiyama, T.; Uchiro, H. ; Shiina, I.; Kobayashi, S., Chem. Lett. 1990 ; 1019-1022.
9. Mikami, K; Terada, M.; Nakai, T., J. Am. Chem. Soc. 1990; 112 : 3949-3954; Mukaiyama, T.; Uchiro, H. ; Shiina, I.; Kobayashi, S., Chem. Lett. 1990 ; 1019-1022.
10. 4 as catalyst ; see [1].
11. 19F NMR resonances of the (S)-and (R)-MTPA esters derivatives. 2 Also the diastereofacial selectivity for the major anti isomer is consistent with the chelation-controlled transition structure.