Stereoselective synthesis of α,α-disubstituted amines by a sequential nucleophilic addition to O-protected cyanohydrins

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1961-1968

  Charette, André B ^a   Gagnon, Alexandre ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOHYDRIN; NITRILE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033591117     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00201-3     Document Type: Article

References (38)

1. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
2. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
3. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
4. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
5. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
6. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
7. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
8. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
9. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
10. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
11. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
12. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
13. Synthesis of α,α-disubstituted α-amino acids: (a) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. (b) Chinchilla, R.; Galindo, N.; Nàjera, C. Tetrahedron: Asymmetry 1998, 9, 2769-2772. (c) O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778. (d) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415. (e) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637. (f) Dyker, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 1700-1702. (g) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225-227. (h) Ferey, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 430-432. (i) Harwood, L. M.; Vines, K. J.; Drew, M. G. B. Synlett 1996, 1051-1053. (j) Studer, A.; Seebach, D. Liebigs Ann. Chem. 1995, 217-222. (k) Obrecht, D.; Spiegler, C.; Schönholzer, P.; Müller, K.; Heimgarther, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666-1696. (l) Schöllkopf, U. Top. Curr. Chem. 1983, 109, 66-84.
14. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268-269.
15. Physical properties of peptides containing α,α-disubstituted α-amino acids: (a) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315-1337. (b) Burgess, K.; Ho, K.-K.; Montgomery Pettitt, B. J. Am. Chem. Soc. 1995, 117, 54-65. (c) Di Blasio, B.; Pavone, V.; Lombardi, A.; Pedone, C.; Benedetti, R. Biopolymers 1993, 33, 1037-1049.
16. Physical properties of peptides containing α,α-disubstituted α-amino acids: (a) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315-1337. (b) Burgess, K.; Ho, K.-K.; Montgomery Pettitt, B. J. Am. Chem. Soc. 1995, 117, 54-65. (c) Di Blasio, B.; Pavone, V.; Lombardi, A.; Pedone, C.; Benedetti, R. Biopolymers 1993, 33, 1037-1049.
17. Physical properties of peptides containing α,α-disubstituted α-amino acids: (a) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315-1337. (b) Burgess, K.; Ho, K.-K.; Montgomery Pettitt, B. J. Am. Chem. Soc. 1995, 117, 54-65. (c) Di Blasio, B.; Pavone, V.; Lombardi, A.; Pedone, C.; Benedetti, R. Biopolymers 1993, 33, 1037-1049.
18. (a) Toniolo, C.; Bonora, G. M.; Bavoso, A; Benedetti, P.; Di Blasio, B.; Pavone, V.; Pedone, C. Biopolymers 1983, 22, 205-215.
19. (b) Huang, Z.; He, Y.-B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. J. Am. Chem. Soc. 1992, 114, 9390-9401.
20. Charette, A. B.; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147-5150.
21. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
22. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
23. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
24. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
25. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
26. For examples of diastereoselective uncatalyzed double nucleophilic additions on cyanohydrins, see: Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525-10535. For examples of racemic uncatalyzed double nucleophilic additions on cyanohydrins, see: (a) Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527. (b) Amouroux, R.; Axiotis, G. P. Synthesis 1981, 270-272. (c) Chastrette, M.; Axiotis, G. P. Synthesis 1980, 889-890. (d) Gauthier, R.; Axiotis, G. P.; Chastrette, M. J. Organomet. Chem. 1977, 140, 245-255. (e) Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 14, 1057-1060.
27. For other methods to access enantioenriched α,α-disubstituted amines, see: Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268-269, and references cited therein.
28. For reviews on TADDOL derivatives and TADDOL titanium complexes, see: Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohac, A.; Ganter, C.; Gawley, R. E.; Kühnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta 1994, 77, 2071-2110.
29. Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1321-1323.
30. The remaining material was the ketone resulting from the hydrolysis of the imine resulting from monoaddition. The absolute configuration was determined by conversion into the N-formyl alcohol: Richter, W. J.; Richter, B.; Ruch, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 30-36.
31. For reviews on binaphthol and binaphthol-titanium complexes, see: Pu, L. Chem. Rev. 1998, 98, 2405.
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