α-Heteroatom-Substituted 1-Alkenyllithium Reagents: Carbanions and Carbenoids for C-C Bond Formation

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 430-451

  Braun, Manfred ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Lithium; Nucleophilic additions; Synthetic methods; Umpolung

Indexed keywords

EID: 0032473448     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<430::aid-anie430>3.0.co;2-5     Document Type: Review

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25. The apparent paradox that the α-carbon atom bears a positive partial charge in vinyl anions can, according to ab initio calculations, be explained by the fact that although the σ electron density is increased at the anionic carbon atom in the transition from ethene to the vinyl anion, a large reduction of the π electron density occurs at the same carbon atom: J. E. Williams, Jr., A. Streitwieser, Jr., J. Am. Chem. Soc. 1975, 97, 2634-2644; see also ref. [10]
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31. In contrast, a crystal structure analysis of 2-lithiobenzofuran · tmeda clearly shows an interaction between the lithium and the oxygen atom: S. Harder, J. Boersma, L. Brandsma, J. A. Kanters, W. Bauer, R. Pi, P. von R. Schleyer, H. Schöllhorn, U. Thewalt, Organometallics 1989, 8, 1688-1696.
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300. See, for example, R. S. Coleman, A. J. Carpenter, Tetrahedron Lett. 1992, 33, 1697-1700; some stereoselective additions to chiral aldehydes with vinyl cuprates have been described: S. D. Burke, A. D. Piscopio, B. E. Marron, M. A. Matulenko, G. Pan, Tetrahedron Lett. 1991, 52, 857-858; P. Metz, A. Schoop, Tetrahedron 1993, 49, 10597-10608; ibid. 1995, 51, 9023-9030.
301. See, for example, R. S. Coleman, A. J. Carpenter, Tetrahedron Lett. 1992, 33, 1697-1700; some stereoselective additions to chiral aldehydes with vinyl cuprates have been described: S. D. Burke, A. D. Piscopio, B. E. Marron, M. A. Matulenko, G. Pan, Tetrahedron Lett. 1991, 52, 857-858; P. Metz, A. Schoop, Tetrahedron 1993, 49, 10597-10608; ibid. 1995, 51, 9023-9030.
302. See, for example, R. S. Coleman, A. J. Carpenter, Tetrahedron Lett. 1992, 33, 1697-1700; some stereoselective additions to chiral aldehydes with vinyl cuprates have been described: S. D. Burke, A. D. Piscopio, B. E. Marron, M. A. Matulenko, G. Pan, Tetrahedron Lett. 1991, 52, 857-858; P. Metz, A. Schoop, Tetrahedron 1993, 49, 10597-10608; ibid. 1995, 51, 9023-9030.
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328. An alternative is shown in the enantioselective enzymatic cyanohydrin formation; cf. F. Effenberger, T. Ziegler, S. Förster, Angew. Chem. 1987, 99, 491-492; Angew. Chem. Int. Ed. Engl. 1987, 26, 458; U. Niedermeyer, M.-R. Kula, Angew. Chem. 1990, 102, 423-425; Angew. Chem. Int. Ed. Engl. 1990, 23, 386-387.
329. An alternative is shown in the enantioselective enzymatic cyanohydrin formation; cf. F. Effenberger, T. Ziegler, S. Förster, Angew. Chem. 1987, 99, 491-492; Angew. Chem. Int. Ed. Engl. 1987, 26, 458; U. Niedermeyer, M.-R. Kula, Angew. Chem. 1990, 102, 423-425; Angew. Chem. Int. Ed. Engl. 1990, 23, 386-387.
330. An alternative is shown in the enantioselective enzymatic cyanohydrin formation; cf. F. Effenberger, T. Ziegler, S. Förster, Angew. Chem. 1987, 99, 491-492; Angew. Chem. Int. Ed. Engl. 1987, 26, 458; U. Niedermeyer, M.-R. Kula, Angew. Chem. 1990, 102, 423-425; Angew. Chem. Int. Ed. Engl. 1990, 23, 386-387.
331. An alternative is shown in the enantioselective enzymatic cyanohydrin formation; cf. F. Effenberger, T. Ziegler, S. Förster, Angew. Chem. 1987, 99, 491-492; Angew. Chem. Int. Ed. Engl. 1987, 26, 458; U. Niedermeyer, M.-R. Kula, Angew. Chem. 1990, 102, 423-425; Angew. Chem. Int. Ed. Engl. 1990, 23, 386-387.
332. L. Colombo, C. Gennari, C. Scolastico, G. Guanti, E. Narisano, J. Chem. Soc. Chem. Commun. 1979, 591-592; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
333. L. Colombo, C. Gennari, C. Scolastico, G. Guanti, E. Narisano, J. Chem. Soc. Chem. Commun. 1979, 591-592; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
334. L. Colombo, C. Gennari, C. Scolastico, G. Guanti, E. Narisano, J. Chem. Soc. Chem. Commun. 1979, 591-592; D. Enders, H. Lotter, Angew. Chem. 1981, 93, 831-832; Angew. Chem. Int. Ed. Engl. 1981, 20, 795-796.
335. See ref. [73], and references therein.
336. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford 1989; J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 300-305; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748, and references therein.
337. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford 1989; J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 300-305; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748, and references therein.
338. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford 1989; J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 300-305; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748, and references therein.
339. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford 1989; J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 300-305; D. Seebach, A. R. Sting, M. Hoffmann, Angew. Chem. 1996, 108, 2880-2921; Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748, and references therein.
340. T. R. Kelly, P. N. Kaul, J. Org. Chem. 1983, 48, 2775-2777.
341. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
342. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
343. Enantiomerically pure vinyl sulfoxides with sulfur as the stereogenic center only lead to high diastereoselectivities in special cases when they react with aldehydes; cf. ref. [56].
344. Formal inversion of configuration due to change in the order of priority.
345. S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford 1991, pp. 585-661; C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422, and references therein.
346. S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford 1991, pp. 585-661; C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422, and references therein.
347. S. A. Godleski in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, Oxford 1991, pp. 585-661; C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422, and references therein.
348. T. Hayashi, A. Yamamoto, T. Hagihara, J. Org. Chem. 1986, 51, 723-727.
349. M. Braun, C. Unger, unpublished results.
350. G. Kresze, R. Albrecht, Angew. Chem. 1962, 74, 781-782; Angew. Chem. Int. Ed. Engl. 1962, 1, 595-596; R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489; G. Kresze, W. Wucherpfennig, Angew. Chem. 1967, 79, 109-127; Angew. Chem. Int. Ed. Engl. 1967, 6, 149-167.
351. G. Kresze, R. Albrecht, Angew. Chem. 1962, 74, 781-782; Angew. Chem. Int. Ed. Engl. 1962, 1, 595-596; R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489; G. Kresze, W. Wucherpfennig, Angew. Chem. 1967, 79, 109-127; Angew. Chem. Int. Ed. Engl. 1967, 6, 149-167.
352. G. Kresze, R. Albrecht, Angew. Chem. 1962, 74, 781-782; Angew. Chem. Int. Ed. Engl. 1962, 1, 595-596; R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489; G. Kresze, W. Wucherpfennig, Angew. Chem. 1967, 79, 109-127; Angew. Chem. Int. Ed. Engl. 1967, 6, 149-167.
353. G. Kresze, R. Albrecht, Angew. Chem. 1962, 74, 781-782; Angew. Chem. Int. Ed. Engl. 1962, 1, 595-596; R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489; G. Kresze, W. Wucherpfennig, Angew. Chem. 1967, 79, 109-127; Angew. Chem. Int. Ed. Engl. 1967, 6, 149-167.
354. G. Kresze, R. Albrecht, Angew. Chem. 1962, 74, 781-782; Angew. Chem. Int. Ed. Engl. 1962, 1, 595-596; R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489; G. Kresze, W. Wucherpfennig, Angew. Chem. 1967, 79, 109-127; Angew. Chem. Int. Ed. Engl. 1967, 6, 149-167.
355. Cf. K. Griesbaum, H. Keul, Angew. Chem. 1975, 87, 748-749; Angew. Chem. Int. Ed. Engl. 1975, 14, 716.
356. Cf. K. Griesbaum, H. Keul, Angew. Chem. 1975, 87, 748-749; Angew. Chem. Int. Ed. Engl. 1975, 14, 716.
357. J. Kovacs, U. R. Ghatak, J. Org. Chem. 1966, 31, 119-121; J. Rudinger, H. M. van den Brink-Zimmermannová, Helv. Chim. Acta 1973, 56, 2216-2226; S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, J. Am. Chem. Soc. 1967, 89, 5311-5312; review: I. Schön, Chem Rev. 1984, 84, 287-297.
358. J. Kovacs, U. R. Ghatak, J. Org. Chem. 1966, 31, 119-121; J. Rudinger, H. M. van den Brink-Zimmermannová, Helv. Chim. Acta 1973, 56, 2216-2226; S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, J. Am. Chem. Soc. 1967, 89, 5311-5312; review: I. Schön, Chem Rev. 1984, 84, 287-297.
359. J. Kovacs, U. R. Ghatak, J. Org. Chem. 1966, 31, 119-121; J. Rudinger, H. M. van den Brink-Zimmermannová, Helv. Chim. Acta 1973, 56, 2216-2226; S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, J. Am. Chem. Soc. 1967, 89, 5311-5312; review: I. Schön, Chem Rev. 1984, 84, 287-297.
360. J. Kovacs, U. R. Ghatak, J. Org. Chem. 1966, 31, 119-121; J. Rudinger, H. M. van den Brink-Zimmermannová, Helv. Chim. Acta 1973, 56, 2216-2226; S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, J. Am. Chem. Soc. 1967, 89, 5311-5312; review: I. Schön, Chem Rev. 1984, 84, 287-297.
361. T. Mukaiyama, Org. React. N. Y. 1982, 28, 203-331.
362. N. Risch, M. Arend, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E 21b, pp. 1848-1852, and references therein.
363. T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099-1102; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023-1025, and references therein.
364. T. Rein, R. Kreuder, P. von Zezschwitz, C. Wulff, O. Reiser, Angew. Chem. 1995, 107, 1099-1102; Angew. Chem. Int. Ed. Engl. 1995, 34, 1023-1025, and references therein.