Enantiotopic group recognition: Direct evidence for selective complexation of enantiotopic groups by a chiral host

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages 4494-4495

  Reetz, Manfred T ^a   Rudolph, Joachim ^a   Mynott, Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; HYDROGEN BOND; MOLECULAR RECOGNITION; NONHUMAN; PHYSICAL PHENOMENA;

EID: 17544382753     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954183e     Document Type: Article

References (28)

1. (a) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995.
2. (b) Vögtle, F. Supramolecular Chemistry; Wiley: Chichester/England, 1991.
3. (a) Webb, T. H.; Wilcox, C. S. Chem. Soc. Rev. 1993, 22, 383.
4. (b) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823.
5. (a) Terradas, F.; Teston-Henry, M.; Fitzpatrick, P. A.; Klibanov, A. M. J. Am. Chem. Soc. 1993, 115, 390.
6. (b) Jones, J. B. Aldrichimica Acta 1993, 26, 105.
7. (c) Faber, K. Biotransformations in Organic Chemistry; Springer: Berlin, 1992.
8. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
9. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
10. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
11. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
12. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
13. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
14. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
15. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
16. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
17. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
18. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
19. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
20. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. (l) Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
21. Typical examples: (a) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem. 1971, 83, 492: Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (c) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1. (d) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327. (e) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323. (f) Harada, T.; Wada, I.; Oku, A. J. Org. Chem. 1989, 54, 2599. (g) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1990, 46, 4793. (h) Mikami, K.; Narisawa, S.; Shimizu, M.; Terada, M. J. Am. Chem. Soc. 1992, 114, 6566. (i) Takemoto, T.; Sodeoka, M; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477. (j) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1994, 611. (k) Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, A.; van Basten, A. J. Am. Chem. Soc. 1994, 116, 4507. Seebach, D.; Jaeschke, G.; Wang, Y. M. Angew. Chem. 1995, 107, 2605; Angew. Chem., Int. Ed. Engl. 1995, 34, 2395.
22. Izatt, R. M.; Zhu, C. Y.; Dolley, N. K.; Curtis, J. C.; Kou, X.; Bradshaw, J. S. J. Phys. Org. Chem. 1992, 5, 656.
23. 1)": Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 703. See also the earlier discussion by Jaffé, H. H.; Orchin, M. Symmetry in Chemistry; Wiley: New York, 1965; p 25.
24. 1)": Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 703. See also the earlier discussion by Jaffé, H. H.; Orchin, M. Symmetry in Chemistry; Wiley: New York, 1965; p 25.
25. (b) It should be noted that even such molecules as n-butane have chiral conformations. See also discussion on chiramers of ethane: Zabrodsky, H.; Peleg, S.; Avnir, D. J. Am. Chem. Soc. 1993, 115, 8278.
26. (a) Mynott, R. unpublished results.
27. (b) Rudolph, J. Dissertation, Universität Bochum, 1995.
28. + group is equatorial.