Allylic stereocontrol of the intramolecular diels-alder reaction

Chemistry - A European Journal

Volumn 11, Issue 8, 2005, Pages 2525-2536

  Lilly, Michael J ^a   Miller, Natalie A ^b   Edwards, Alison J ^b   Willis, Anthony C ^b   Turner, Peter ^c   Paddon Row, Michael N ^d   Sherburn, Michael S ^b  

^a MASSEY UNIVERSITY   (New Zealand)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^c UNIVERSITY OF SYDNEY   (Australia)

^d UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Chiral pool; Cyclo addition; Density functional calculations; Diastereoselectivity; Synthetic methods

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; DERIVATIVES; ESTERS; ISOMERS; MATHEMATICAL MODELS; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS; SUBSTRATES; SYNTHESIS (CHEMICAL);

CHIRAL POOL; CYCLOADDITION; DENSITY FUNCTIONAL CALCULATIONS; DIASTEREOSELECTIVITY; SYNTHETIC METHODS;

REACTION KINETICS;

ASCORBIC ACID; LACTIC ACID; MALIC ACID; MALIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER; STEREOISOMERISM;

ASCORBIC ACID; COMPUTERS; LACTIC ACID; MALATES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 17544372783     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401215     Document Type: Article

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77. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
78. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
79. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
80. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
81. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
82. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
83. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
84. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
85. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
86. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
87. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
88. For synthetic studies on IMDA reactions of pentadienyl maleates and fumarates, see: a) S.D. Burke, S.M. Smith Strickland, T.H. Powner, J. Org. Chem. 1983, 48, 454-459; b)P. R. Jenkins, K. A. Menear, P. Barraclough, M. S. Nobbs, J. Chem. Soc. Chem. Commun. 1984, 1423-1424; c) P. Magnus, C. Walker, P. R. Jenkins, K. A. Menear, Tetrahedron Lett. 1986, 27, 651 -654; d) M. K. Eberle, H. P. Weber, J. Org. Chem. 1988, 53, 231 -235; e) J. F. He, Y. L. Wu, Tetrahedron 1988, 44, 1933-1940; f) M. J. Batchelor, J. M. Mellor, J. Chem. Soc. Perkin Trans. 1 1989, 985-995; g) J. Becher, H. C. Nielsen, J. P. Jacobsen, O. Simonsen, H. Clausen, J. Org. Chem. 1988, 53, 1862-1871; h) M. Toyota, Y. Wada, K. Fukumoto, Heterocycles 1993, 35, 111-114; i) L. Berthon, A. Tahri, D. Uguen, Tetrahedron Lett. 1994, 35, 3937-3940; j) K. Takatori, K. Hasegawa, S. Narai, M. Kajiwar, Heterocycles 1996, 42, 525-528; k)S. Arseniyadis, R. Brondi-Alves, D. V. Yashunsky, P. Potier, L. Toupet, Tetrahedron 1997, 53, 1003-1014; 1) T. N. Cayzer, M. N. Paddon-Row, D. Moran, A. D. Payne, M. S. Sherburn, P. Turner, J. Org. Chem. submitted.
89. The IMDA reaction of the corresponding 2-butynoate ester was thwarted by cycloadduct aromatization under the reaction conditions.
90. M. N. Paddon-Row, N. G. Rondan, K. N. Houk, J. Am. Chem. Soc. 1982, 104, 7162-7166.
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92. All TSs were fully optimized and characterized by harmonic frequency calculations. The Gaussian 98 package was used for all calculations: M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Monlgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, in Gaussian 98, Revision A.11, Gaussian, Inc., Pittsburgh PA, 2001.
93. Each TS was fully optimized - that is, no geometrical constraints were imposed - and characterized by carrying out a harmonic vibrational frequency calculation. In principle, each TS corresponding to a particular conformation about the C*-Cl bond (torsional angle ψ) is capable of exhibiting conformational isomerism about the C*O bond (torsional angle θ), there being three such isomers. These three C*-O conformational isomeric TSs were not fully optimized for reasons of computational economy. Instead, for each TS which was optimized with respect to θ, a potential energy curve was calculated with respect to θ. For each value of θ of this scan, the geometry of the molecule was fully optimized with the exception that the forming bonds between the diene and dienophile were frozen at the values corresponding to those typically found for this type of IMDA TS. Such a potential energy scan resulted in the location of three energy minima corresponding to three different values of θ. The geometry corresponding to the lowest energy minimum was then fully optimized - with no geometrical constraints imposed - to give the TS corresponding to that value of θ. Although the TSs corresponding to the other two values of θ were neither optimized, nor further considered, our procedure almost certainly guarantees that we have located the lowest energy TS conformation for that particular value of ψ. The fact that we obtain such good agreement between the experimental and computational selcctivities strongly suggests that our procedure is a valid one.
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