5546
Chem., Int. Ed. Engl. 1997, 36, 2507. (d) Ooi, T.; Saito, A.; Maruoka, K. Tetrahedron Lett. 1998, 39, 3745. (e) Ooi,
T.; Miura, T.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 2347.
2. For reviews of Lewis acid chemistry, see: (a) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis;
Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1.10, p. 283.
(b) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1995.
3. In the synthesis of a mono-Zr reagent, 2 equiv. of 3-t-butyl-2-hydroxy-5-methylbenzophenone is incorporated,
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whether 0.5 or 1 equiv. of Zr(OPr )4 Pr OH is present, to furnish fully-coordinated 3 as a sole product, which still
has a coordination ability toward carbonyl substrates by ligand exchange as ascertained by 13C NMR analysis.
For similar argument, see Ref 1.
4. Asymmetric stoichiometric allylations: Allenylboranes: (a) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983,
105, 2092. (b) Short, R. P.; Masamune, S. J. Am. Chem. Soc. 1989, 111, 1892. (c) Racherla, U. S.; Brown, H. C.
J. Org. Chem. 1991, 56, 401. Allylboronates: (d) Herold, T.; Homann, R. W. Angew. Chem., Int. Ed. Engl. 1978,
17, 768. (e) Homann, R. W.; Herold, T. Chem. Ber. 1981, 114, 375. (f) Roush, W. R.; Walts, A. E.; Hoong, L. K.
J. Am. Chem. Soc. 1985, 107, 8186. (g) Roush, W. R.; Ban®, L. J. Am. Chem. Soc. 1988, 110, 3979. (h) Roush,
W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109. See also: (i) Reetz, M. T.; Zierke,
T. Chem. Ind. 1988, 663. Allylboradiazolidines: (j) Corey, E. J.; Yu, C.-M.; Kim, S. S. J. Am. Chem. Soc. 1989,
111, 5495. Allyltitanates: (k) Riediker, M.; Duthaler, R. O. Angew. Chem., Int. Ed. Engl. 1989, 28, 494. (l)
Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99. (m) Hafner, A.; Duthaler, R. O.; Marti, R.;
Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. Allylaluminum derivatives: (n)
Minowa, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1987, 60, 3697. Allylstannanes: (o) Otera, J.; Kawasaki, Y.;
Mizuno, H.; Shimizu, Y. Chem. Lett. 1983, 1529. (p) Otera, J.; Yoshinaga, Y.; Yamaji, T.; Yoshioka, T.;
Kawasaki, Y. Organometallics 1985, 4, 1213. (q) Boldrini, G. P.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A.
J. Chem. Soc., Chem. Commun. 1986, 685. (r) Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Tarasco, C.; Trombini, C.;
Umani-Ronchi, A. J. Org. Chem. 1987, 52, 5447. (s) Boga, C.; Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-
Ronchi, A. J. Organomet. Chem. 1988, 353, 177.
5. Asymmetric catalytic allylations: CAB complex: (a) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561. (b)
Marshall, J. A.; Tang, Y. Synlett 1992, 653. (c) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K;
Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. BINOL/Ti(IV) complex: (d) Aoki, S.; Mikami, K.; Terada,
M.; Nakai, T. Tetrahedron 1993, 49, 1783. (e) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-
Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001. (f) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc.
1993, 115, 8467. (g) Kech, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7872. (h) Keck, G. E.; Krishnamurthy,
D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543. (i) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett.
1994, 35, 8323. (j) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217. (k) Gauthier Jr., D. R.;
Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2363. (l) Weigand, S.; Bruckner, R. Chem. Eur. J. 1996, 2,
1077. (m) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095. (n) Yu, C.-M.; Choi,
H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. Chem. Commun. 1997, 761. (o) Yu, C.-M.; Choi, H.-S.; Yoon, S.-K.; Jung,
W.-H. Synlett 1997, 889. BINAP/AgOTf complex: (p) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H.
J. Am. Chem. Soc. 1996, 118, 4723. Bis(oxazoline)/Zn(II) complex: (q) Cozzi, P. G.; Orioli, P.; Tagliavini, E.;
Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145. Bis(oxazoline)/Rh(II) complex: (r) Motoyama, Y.; Narusawa,
H.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1999, 131.
6. Asymmetric catalytic allylations with chiral Zr catalysts: Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.;
Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897.
7. The corresponding chiral mono-Zr catalyst was prepared by simply mixing of 3-t-butyl-2-hydroxy-5-
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methylbenzophenone, (S)-binaphthol, and Zr(OPr )4 Pr OH in an equimolar ratio in CH2Cl2.