The unexpected reorganizations of a β-lactone aldolate to 1,3-dioxan-4- ones in the reaction of 4-(1-methylethyl)-3-[(phenylthio)methyl]-1-oxetan-2- one lithium enolate with acetaldehyde

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2529-2533

  Nava Salgado, Víctor Oswaldo ^a   Adam, Waldemar ^b  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Aldehydes; Aldol reactions; Lactones; Lithium enolates; Lactone aldolate

Indexed keywords

ACETALDEHYDE; LACTONE DERIVATIVE; LITHIUM DERIVATIVE;

ARTICLE; CATALYSIS; MOLECULAR DYNAMICS; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; SYNTHESIS;

EID: 0033868638     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2529::aid-ejoc2529>3.3.co;2-3     Document Type: Article

References (40)

1. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
2. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
3. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
4. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
5. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
6. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
7. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
8. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
9. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
10. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
11. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
12. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
13. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
14. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
15. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
16. For recent reviews of β-lactone chemistry, see: H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403-6434; A. Pommier, J.-M. Pons, Synthesis 1993, 441-459. For lead references on β-lactone chemistry, see: J. A. Marshall, H. Faubl, J. Am. Chem. Soc. 1970, 92, 948-955; W. Adam, J. Baeza, J.-C. Liu, J. Am. Chem. Soc. 1972, 94, 2000-2006; S. Mageswaran, M. U. S. Sultanbawa, J. Chem. Soc., Perkin Trans. 1 1976, 884-890; B. Ganem, G. W. Holbert, L. B. Weiss, K. Ishizumi, J. Am. Chem. Soc. 1978, 100, 6483-6491; J. Mulzer, A. Pointer, A. Chucholowski, G. Brüntrup, J. Chem. Soc., Chem. Commun. 1979, 52-54; J. I. Luengo, M. Koreeda, Tetrahedron Lett. 1984, 25, 4881-4884; G. E. Renzoni, T. K. Yin, F. Miyake, W. T. Borden, Tetrahedron 1986, 42, 1581-1584; R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327; C. Palomo, J. I. Miranda, A. Linden, J. Org. Chem. 1996, 61, 9196-9201; A. M. Warshawsky, M. V. Patel, T.-M. Chen, J. Org. Chem. 1997, 62, 6439-6440; O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642; H. W. Yang, D. Romo, Tetrahedron Lett. 1998, 39, 2877-2880; F. Machrouhi, J. L. Namy, Tetrahedron 1998, 54, 11111-11122; M. Shindo, Y. Sato, K. Shishido, J. Am. Chem. Soc. 1999, 121, 6507-6508.
17. J. Mulzer, T. Kerkmann, J. Am. Chem. Soc. 1980, 102, 3620-3622; J. Mulzer, A. Chucholowski, O. Lammer, I. Jibril, G. Huttner, J. Chem. Soc., Chem. Commun. 1983, 869-871; A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1320-1325; R. L. Danheiser, J. S. Nowick, J. Org. Chem. 1991, 56, 1176-1185.
18. J. Mulzer, T. Kerkmann, J. Am. Chem. Soc. 1980, 102, 3620-3622; J. Mulzer, A. Chucholowski, O. Lammer, I. Jibril, G. Huttner, J. Chem. Soc., Chem. Commun. 1983, 869-871; A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1320-1325; R. L. Danheiser, J. S. Nowick, J. Org. Chem. 1991, 56, 1176-1185.
19. J. Mulzer, T. Kerkmann, J. Am. Chem. Soc. 1980, 102, 3620-3622; J. Mulzer, A. Chucholowski, O. Lammer, I. Jibril, G. Huttner, J. Chem. Soc., Chem. Commun. 1983, 869-871; A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1320-1325; R. L. Danheiser, J. S. Nowick, J. Org. Chem. 1991, 56, 1176-1185.
20. J. Mulzer, T. Kerkmann, J. Am. Chem. Soc. 1980, 102, 3620-3622; J. Mulzer, A. Chucholowski, O. Lammer, I. Jibril, G. Huttner, J. Chem. Soc., Chem. Commun. 1983, 869-871; A. Griesbeck, D. Seebach, Helv. Chim. Acta 1987, 70, 1320-1325; R. L. Danheiser, J. S. Nowick, J. Org. Chem. 1991, 56, 1176-1185.
21. W. Adam, L. Hasemann, V. O. Nava-Salgado, B. Nestler, E.-M. Peters, K. Peters, F. Prechtl, H. G. von Schnering, J. Org. Chem. 1991, 56, 5782-5785; W. Adam, V. O. Nava-Salgado, E.-M. Peters, K. Peters, H. G. von Schnering, Chem. Ber. 1993, 126, 1481-1486; W. Adam, L. Hasemann, Chem. Ber. 1990, 123, 1449-1451; W. Adam, L. Hasemann, Tetrahedron Lett. 1991, 32, 7033-7036.
22. W. Adam, L. Hasemann, V. O. Nava-Salgado, B. Nestler, E.-M. Peters, K. Peters, F. Prechtl, H. G. von Schnering, J. Org. Chem. 1991, 56, 5782-5785; W. Adam, V. O. Nava-Salgado, E.-M. Peters, K. Peters, H. G. von Schnering, Chem. Ber. 1993, 126, 1481-1486; W. Adam, L. Hasemann, Chem. Ber. 1990, 123, 1449-1451; W. Adam, L. Hasemann, Tetrahedron Lett. 1991, 32, 7033-7036.
23. W. Adam, L. Hasemann, V. O. Nava-Salgado, B. Nestler, E.-M. Peters, K. Peters, F. Prechtl, H. G. von Schnering, J. Org. Chem. 1991, 56, 5782-5785; W. Adam, V. O. Nava-Salgado, E.-M. Peters, K. Peters, H. G. von Schnering, Chem. Ber. 1993, 126, 1481-1486; W. Adam, L. Hasemann, Chem. Ber. 1990, 123, 1449-1451; W. Adam, L. Hasemann, Tetrahedron Lett. 1991, 32, 7033-7036.
24. W. Adam, L. Hasemann, V. O. Nava-Salgado, B. Nestler, E.-M. Peters, K. Peters, F. Prechtl, H. G. von Schnering, J. Org. Chem. 1991, 56, 5782-5785; W. Adam, V. O. Nava-Salgado, E.-M. Peters, K. Peters, H. G. von Schnering, Chem. Ber. 1993, 126, 1481-1486; W. Adam, L. Hasemann, Chem. Ber. 1990, 123, 1449-1451; W. Adam, L. Hasemann, Tetrahedron Lett. 1991, 32, 7033-7036.
25. [4] W. Adam, V. O. Nava-Salgado, B. Wegener, E. Winterfeld, Chem. Ber. 1993, 126, 1509-1510; W. Adam, P. Groer, C. R. Saha-Moeller, Tetrahedron: Asymmetry 1997, 8, 833-836.
26. [4] W. Adam, V. O. Nava-Salgado, B. Wegener, E. Winterfeld, Chem. Ber. 1993, 126, 1509-1510; W. Adam, P. Groer, C. R. Saha-Moeller, Tetrahedron: Asymmetry 1997, 8, 833-836.
27. W. Adam, V. O. Nava-Salgado, J. Org. Chem. 1995, 60, 578-584.
28. V. O. Nava-Salgado, E.-M. Peters, K. Peters, H. G. von Schnering, W. Adam, J. Org. Chem. 1995, 60, 3879-3886.
29. J. Mulzer, T. Kerkmann, Angew. Chem. Int. Ed. Engl. 1980, 19, 466-468; Angew. Chem. 1980, 92, 470-471.
30. J. Mulzer, T. Kerkmann, Angew. Chem. Int. Ed. Engl. 1980, 19, 466-468; Angew. Chem. 1980, 92, 470-471.
31. J. Mulzer, T. Kerkmann, J. Am. Chem. Soc. 1980, 102, 3620-3622.
32. J. Mulzer, A. Chucholowski, Angew. Chem. Int. Ed. Engl. 1982, 21, 777-778; Angew. Chem. 1982, 94, 788-789.
33. J. Mulzer, A. Chucholowski, Angew. Chem. Int. Ed. Engl. 1982, 21, 777-778; Angew. Chem. 1982, 94, 788-789.
34. D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448-464; D. Seebach, R. Imwinkelried, G. Stucky, Angew. Chem. Int. Ed. Engl. 1986, 25, 178-180; Angew. Chem. 1986, 95, 182-184.
35. D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448-464; D. Seebach, R. Imwinkelried, G. Stucky, Angew. Chem. Int. Ed. Engl. 1986, 25, 178-180; Angew. Chem. 1986, 95, 182-184.
36. D. Seebach, R. Imwinkelried, G. Stucky, Helv. Chim. Acta 1987, 70, 448-464; D. Seebach, R. Imwinkelried, G. Stucky, Angew. Chem. Int. Ed. Engl. 1986, 25, 178-180; Angew. Chem. 1986, 95, 182-184.
37. D. A. Evans, J. V. Nelson, T. R. Taber, Top. Stereochem. 1982, 13, 1-115; T. Mukaiyama, Org. React. 1982, 28, 203-331; C. H. Heathcock, in Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York. 1984; Vol. 3, Chapter 2, pp 111-212.
38. D. A. Evans, J. V. Nelson, T. R. Taber, Top. Stereochem. 1982, 13, 1-115; T. Mukaiyama, Org. React. 1982, 28, 203-331; C. H. Heathcock, in Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York. 1984; Vol. 3, Chapter 2, pp 111-212.
39. D. A. Evans, J. V. Nelson, T. R. Taber, Top. Stereochem. 1982, 13, 1-115; T. Mukaiyama, Org. React. 1982, 28, 203-331; C. H. Heathcock, in Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York. 1984; Vol. 3, Chapter 2, pp 111-212.
40. J.-M. Lapierre, M. Gautschi, G. Greiveldinger, D. Seebach, Chem. Ber. 1993, 126, 2739-2746.