Cyclic BF2 adducts of functionalized fischer vinylcarbene complexes: Preparation and stereoselective Diels-Alder reactions with 2-amino 1,3- dienes

Journal of the American Chemical Society

Volumn 120, Issue 11, 1998, Pages 2514-2522

  Barluenga, José ^a   Canteli, Rosa María ^a   Flórez, Josefa ^a   García Granda, Santiago ^a   Gutiérrez Rodríguez, Angel ^a   Martín, Eduardo ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; METAL COMPLEX;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032565134     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972588o     Document Type: Article

References (130)

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90. 2 chelates of β-diketones, β-hydroxy ketones, enamino ketones and 1,3-diamino derivatives are known. See, for example: (a) Brown, N. M. D.; Bladon, P. J. Chem. Soc. A 1969, 526. (b) Itoh, K.; Okazaki, K.; Sera, A.; Chow, Y. L. J. Chem. Soc., Chem. Commun. 1992, 1608. (c) Morris, J.; Wishka, D. G.; Fang, Y. J. Org. Chem. 1992, 57, 6502. (d) Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599.
91. 2 chelates of β-diketones, β-hydroxy ketones, enamino ketones and 1,3-diamino derivatives are known. See, for example: (a) Brown, N. M. D.; Bladon, P. J. Chem. Soc. A 1969, 526. (b) Itoh, K.; Okazaki, K.; Sera, A.; Chow, Y. L. J. Chem. Soc., Chem. Commun. 1992, 1608. (c) Morris, J.; Wishka, D. G.; Fang, Y. J. Org. Chem. 1992, 57, 6502. (d) Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599.
92. 2 chelates of β-diketones, β-hydroxy ketones, enamino ketones and 1,3-diamino derivatives are known. See, for example: (a) Brown, N. M. D.; Bladon, P. J. Chem. Soc. A 1969, 526. (b) Itoh, K.; Okazaki, K.; Sera, A.; Chow, Y. L. J. Chem. Soc., Chem. Commun. 1992, 1608. (c) Morris, J.; Wishka, D. G.; Fang, Y. J. Org. Chem. 1992, 57, 6502. (d) Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599.
93. 2 chelates of β-diketones, β-hydroxy ketones, enamino ketones and 1,3-diamino derivatives are known. See, for example: (a) Brown, N. M. D.; Bladon, P. J. Chem. Soc. A 1969, 526. (b) Itoh, K.; Okazaki, K.; Sera, A.; Chow, Y. L. J. Chem. Soc., Chem. Commun. 1992, 1608. (c) Morris, J.; Wishka, D. G.; Fang, Y. J. Org. Chem. 1992, 57, 6502. (d) Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599.
94. For conventional Fischer vinylcarbene complexes with a fixed s-cis conformation, see: (a) Casey, C. P.; Brunsvold, W. R. J. Organomet. Chem. 1975, 102, 175. (b) Barrett, A. G. M.; Mortier, J.; Sabat, M.; Sturgess, M. A. Organometallics 1988, 7, 2553. (c) Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Gazz. Chim. Ital. 1993, 123, 31. (d) Baldoli, C.; Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Organometallics 1993, 12, 2994. See also ref. 7d.
95. For conventional Fischer vinylcarbene complexes with a fixed s-cis conformation, see: (a) Casey, C. P.; Brunsvold, W. R. J. Organomet. Chem. 1975, 102, 175. (b) Barrett, A. G. M.; Mortier, J.; Sabat, M.; Sturgess, M. A. Organometallics 1988, 7, 2553. (c) Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Gazz. Chim. Ital. 1993, 123, 31. (d) Baldoli, C.; Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Organometallics 1993, 12, 2994. See also ref. 7d.
96. For conventional Fischer vinylcarbene complexes with a fixed s-cis conformation, see: (a) Casey, C. P.; Brunsvold, W. R. J. Organomet. Chem. 1975, 102, 175. (b) Barrett, A. G. M.; Mortier, J.; Sabat, M.; Sturgess, M. A. Organometallics 1988, 7, 2553. (c) Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Gazz. Chim. Ital. 1993, 123, 31. (d) Baldoli, C.; Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Organometallics 1993, 12, 2994. See also ref. 7d.
97. For conventional Fischer vinylcarbene complexes with a fixed s-cis conformation, see: (a) Casey, C. P.; Brunsvold, W. R. J. Organomet. Chem. 1975, 102, 175. (b) Barrett, A. G. M.; Mortier, J.; Sabat, M.; Sturgess, M. A. Organometallics 1988, 7, 2553. (c) Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Gazz. Chim. Ital. 1993, 123, 31. (d) Baldoli, C.; Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Organometallics 1993, 12, 2994. See also ref. 7d.
98. -1, F(000) = 556. Final conventional R = 0.049 and wR2 = 0.121 for 2817 "observed" reflections and 393 variables, GOF -0.909. Red crystal, size 0.29 × 0.19 × 0.13 mm. One strong intramolecular H-bonding interaction was found, showing bond distances N-H - 0.83(4) Å, O⋯H = 1.89(4) Å [N⋯O = 2.614(6) Å] and bond angle N-H⋯O = 144.(3)°.
99. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1582. (b) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. The [4 + 2] cycloadditions of 2-amino-1,3-dienes with conventional tungsten vinylalkoxycarbene complexes have been reported in ref 17c,f.
100. Reviews: (a) Krohn, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1582. (b) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. The [4 + 2] cycloadditions of 2-amino-1,3-dienes with conventional tungsten vinylalkoxycarbene complexes have been reported in ref 17c,f.
101. The isomerization of a tetrasubstituted enamine into the corresponding trisubstituted derivative is a well-known process: (a) Johnson, F. Chem. Rev. 1968, 68, 375. (b) Marc, G.; Nitti, P.; Pitacco, G.; Pizzioli, A.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1997, 223.
102. The isomerization of a tetrasubstituted enamine into the corresponding trisubstituted derivative is a well-known process: (a) Johnson, F. Chem. Rev. 1968, 68, 375. (b) Marc, G.; Nitti, P.; Pitacco, G.; Pizzioli, A.; Valentin, E. J. Chem. Soc., Perkin Trans. 1 1997, 223.
103. -1, F(000) = 2288. Final conventional R = 0.054 and wR2 = 0.155 for 3415 "observed" reflections and 392 variables, GOF = 0.965. Red crystal, size 0.39 × 0.26 × 0.20 mm.
104. -1, F(000) = 1280. Final conventional R = 0.047 and wR2 = 0.125 for 3053 "observed" reflections and 451 variables, GOF = 0.941. Red crystal, size 0.26 × 0.26 × 0.16 mm.
105. (a) Fischer, E. O.; Plabst, D. Chem. Ber. 1974, 107, 3326.
106. (b) Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. J. Chem. Soc., Chem. Commun. 1991, 437.
107. (c) Barluenga, J.; Montserrat, J. M.; Flórez, J.; García-Granda, S.; Martín, E. Chem. Eur. J. 1995, 1, 236.
108. For conventional spirocyclic Fischer carbene complexes, see: (a) Baldoli, C.; Del Buttero, P.; Licandro, E.; Maiorana, S.; Papagni, A.; Zanotti-Gerosa, A. J. Organomet. Chem. 1994, 476, C27. (b) Dötz, K. H.; Neuss, O.; Nieger, M. Synlett 1996, 995. (c) Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617. See also ref 19f.
109. For conventional spirocyclic Fischer carbene complexes, see: (a) Baldoli, C.; Del Buttero, P.; Licandro, E.; Maiorana, S.; Papagni, A.; Zanotti-Gerosa, A. J. Organomet. Chem. 1994, 476, C27. (b) Dötz, K. H.; Neuss, O.; Nieger, M. Synlett 1996, 995. (c) Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617. See also ref 19f.
110. For conventional spirocyclic Fischer carbene complexes, see: (a) Baldoli, C.; Del Buttero, P.; Licandro, E.; Maiorana, S.; Papagni, A.; Zanotti-Gerosa, A. J. Organomet. Chem. 1994, 476, C27. (b) Dötz, K. H.; Neuss, O.; Nieger, M. Synlett 1996, 995. (c) Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617. See also ref 19f.
111. For a review regarding the asymmetric creation of quaternary carbon centers, see: Fuji, K. Chem. Rev. 1993, 93, 2037.
112. For a recent asymmetric Diels-Alder reaction of a chiral 1-amino-3-siloxy-1,3-butadiene leading to cyclohexenones with a quaternary chiral center, see: Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1997, 119, 7165.
113. Indeed, when under analogous reaction conditions carbene complex 7a was treated with the Z isomer of diene 27a, a 2.5:1 mixture of two open-chain diastereomeric keto aldehydes resulting from an initial Michael-type addition of the diene enaminic carbon to the β carbon of the vinylcarbene complex was obtained. These results will be reported separately. See also ref 17f.
114. For chiral 2-amino 1,3-dienes 27 has been assumed to be of lower energy since the conformation in which the alkoxymethyl side chain of the chiral auxiliary is located as far away as possible from the methyl group at the C-3 position: (a) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242. (b) Barluenga. J.; Aznar, F.; Martín, A.; Vázquez, J. T. J. Am. Chem. Soc. 1995, 117, 9419. (c) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M. P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805.
115. For chiral 2-amino 1,3-dienes 27 has been assumed to be of lower energy since the conformation in which the alkoxymethyl side chain of the chiral auxiliary is located as far away as possible from the methyl group at the C-3 position: (a) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242. (b) Barluenga. J.; Aznar, F.; Martín, A.; Vázquez, J. T. J. Am. Chem. Soc. 1995, 117, 9419. (c) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M. P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805.
116. For chiral 2-amino 1,3-dienes 27 has been assumed to be of lower energy since the conformation in which the alkoxymethyl side chain of the chiral auxiliary is located as far away as possible from the methyl group at the C-3 position: (a) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242. (b) Barluenga. J.; Aznar, F.; Martín, A.; Vázquez, J. T. J. Am. Chem. Soc. 1995, 117, 9419. (c) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M. P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805.
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