Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides

Chemistry - A European Journal

Volumn 5, Issue 7, 1999, Pages 2055-2068

  Norsikian, Stephanie ^b   Marek, Ilan ^a   Klein, Sophie ^b   Poisson, Jean F ^b   Normant, Jean F ^b  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b CNRS   (France)

Author keywords

( ) sparteine; Asymmetric catalysis; Carbolithiation; Cyclopropane; Organolithium compounds

Indexed keywords

CYCLOPROPANE DERIVATIVE; ORGANOLITHIUM COMPOUND; SPARTEINE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CHIRALITY; NONHUMAN; STEREOCHEMISTRY; STOICHIOMETRY; THERMODYNAMICS;

EID: 0033021851     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990702)5:7<2055::AID-CHEM2055>3.0.CO;2-9     Document Type: Article

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67. However, when the same reaction was applied to the dimethyl acetal (or the cinnamyl diethylamine) of (Z) sterochemistry, (Z)-8, the opposite enantiomer is effectively obtained; however, the enantioselectivity dropped to only 30%.
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73. When an electrophile (such as MeOD) is added to the benzylic organolithium compound, generated by carbolithiation on β-methylstyrene (no intramolecular chelation), the diastereoselectivity is poor (d.r. = 60:40).
74. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
75. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
76. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
77. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
78. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
79. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
80. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
81. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
82. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
83. For epimerization of carbanionic centers into the thermodynamic product, see: a) P. G. Mc Dougal, B. D. Condon, M. D. Lafosse, Jr., A. M. Lauro, D. Vanderveer, Tetrahedron Lett. 1988, 29, 2547; b) R. Hoffmann, M. Bewersdorf, Tetrahedron Lett. 1990, 31, 67; D. R. Williams, J. G. Philipps, J. C. Huffman, J. Org. Chem. 1981, 46, 4101; A. Krief, M. Hobe, Tetrahedron Lett 1992, 33, 6527; e) A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529; f) P. Beak, J. E. Hunter, Y. M. Jun, A. P. Wallin, J. Am. Chem. Soc 1987, 109, 5403; g) W. H. Miles, S L. Riviera, J. D. Rosario, Tetrahedron Lett. 1992, 33, 305; h) A I. Meyers, J. Guiles, J. S. Warmus, M. A. Gonzales, Tetrahedron Lett. 1991, 32, 5505; W. H. Pearson, A C. Lindbeck, J. Am. Chem Soc. 1991, 113, 8546; j) W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1993, 115, 2622.
84. For a more complete discussion, see: C. Muck-Lichtenfeld, H. Ahlbrecht, Tetrahedron 1996, 52, 10025.
85. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
86. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
87. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
88. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
89. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
90. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
91. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
92. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
93. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
94. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
95. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
96. The formation of cyclopropane by 1,3-elimination between an organogembismetallic and a methoxymethyl ether has already been described. a) I. Marek, D. Beruben, J. F. Normant, Tetrahedron Lett. 1995, 36, 3695; b) D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org Chem. 1995, 60, 2488; D. Beruben, I. Marek, J. F. Normant, N. Platzer. Tetrahedron Lett. 1993, 34, 7575. For some representative formations of chiral cyclopropanes, see: a) A. B. Charette, J.F Marcoux, Synlett 1995, 1197, and references therein; b) J. Salaün, Chem Rev. 1989, 89, 1247, D. Romo, A. I. Meyers, J. Org Chem. 1992, 57, 6265; H. M. L. Davies, N. J. S. Huby, W. R. Cantrell, Jr., J. L. Olive, J. Am. Chem. Soc. 1993, 115, 9468; e) M. P. Doyle in Catalytic Asymmetric Synthesis (Ed : I. Ojima), VCH, New York, 1993; Chapt. 3; f) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339; g) D. A. Evans, K. A. Woerpel, M. J. Scott, Angew. Chem. 1992, 104, 439; Angew. Chem. Int. Ed. Engl. 1992, 31, 430; h) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584.
97. A. Krief, M. Hobe, Tetrahedron Lett. 1992, 33, 6529.
98. For a previous report on the synthesis of chiral cyclopropane mediated by a stoichiometric amount of (-)-sparteine, see: M. Paetow, M. Kotthaus, M. Grehl, R. Fröhlich, D. Hoppe, Synlett 1994, 1034.
99. T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1991, 55, 4986.
100. The correlation was made from the alcohols 30 and 31 by tosylation and displacement with dimethylamine.
101. P. Knochel, R. D. Singer Chem. Rev. 1993, 93, 2117.
102. a) F. Wang, T. Tang, L. Labaudiniere, I. Marek, J. F. Normant, Synlett 1995, 723;
103. b) C. Darcel, F. Flachsmann, P Knochel, Chem. Commun. 1998, 205;
104. c) R. Duddu, M. Eckhardt, M. Furlong, P. Knoess, S. Berger, P. Knochel, Tetrahedron 1994, 50, 2415.
105. d) F. Lhermitte, P. Knochel, Angew. Chem. 1998, 110, 2598; Angew. Chem. Int. Ed. 1998, 37, 2460;
106. d) F. Lhermitte, P. Knochel, Angew. Chem. 1998, 110, 2598; Angew. Chem. Int. Ed. 1998, 37, 2460;
107. e) L Micouin, M. Oestreich, P. Knochel, Angew. Chem. 1997, 109, 274; Angew Chem Int. Ed. Engl. 1997, 36, 245;
108. e) L Micouin, M. Oestreich, P. Knochel, Angew. Chem. 1997, 109, 274; Angew Chem Int. Ed. Engl. 1997, 36, 245;
109. f) Sakami, T. Houkawa, M. Asaoka, H. Takei, J. Chem. Soc. Perkin Trans. 1, 1995, 285;
110. g) T. Houkawa, T. Ueda, S. Sakami, M. Asaoka, H. Takei, Tetrahedron Lett. 1996, 37, 1045.
111. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
112. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
113. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
114. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
115. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
116. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
117. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
118. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
119. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
120. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
121. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
122. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
123. 4]. see: g) D Hoppe, O. Zschage, Angew Chem. 1989, 101, 67; Angew. Chem. Int. Ed. Engl. 1989, 28, 69; h) D. Hoppe, T. Kramer, Tetrahedron Lett. 1987, 28, 5149; B Peschke, J. Lüßmann, M. Dyrbusch, D. Hoppe, Chem. Ber. 1992, 125, 1421. For lithiated benzylic carbamates, see: j) D. Hoppe, A. Carstens, T. Kramer, Angew Chem 1990, 102, 1455; Angew. Chem. Int. Ed. Engl. 1990, 29, 1424. For the benzylic lithium derivatives, see: ref. [10].
124. -C. see: ref. [10].
125. S. Klein, I. Marek, J. F. Normant, J. Org. Chem. 1994, 59, 2925.