Atroposelective synthesis of axially chiral biaryl compounds

Angewandte Chemie - International Edition

Volumn 44, Issue 34, 2005, Pages 5384-5427

  Bringmann, Gerhard ^a   Mortimer, Anne J Price ^a   Keller, Paul A ^b,c   Gresser, Mary J ^b   Garner, James ^b   Breuning, Matthias ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF WOLLONGONG   (Australia)

^c Department of Organic and Medicinal Chemistry ^*

Author keywords

Asymmetric synthesis; Atropisomerism; Axial chirality; Biaryl compounds; Stereoselectivity

Indexed keywords

ASYMMETRIC SYNTHESIS; ATROPISOMERISM; AXIAL CHIRALITY; BIARYL COMPOUNDS; STEREOSELECTIVITY;

CATALYSIS; CHEMICAL BONDS; GROWTH (MATERIALS); STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EID: 24644462889     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462661     Document Type: Review

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217. For a highly atroposelective intermolecular biaryl coupling with a chiral sugar-based scaffold, see: M. Arisawa, S. Ulsumi, M. Nakajima, N. G. Ramesh, H. Tohma, Y. Kita, Chem. Commun. 1999, 469-470.
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229. M. Uemura, H. Nishimura, K. Kamikawa, K. Nakayama, Y. Hayashi, Tetrahedron Lett. 1994, 35, 1909-1912.
230. T. Watanabe, K. Kamikawa, M. Uemura, Tetrahedron Lett. 1995, 36, 6695-6698.
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232. Y. Tanaka, T. Sakamoto, K. Kamikawa, M. Uemura, Synlett 2003, 519-521.
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234. [156a]
235. K. Kamikawa, A. Tachibana, S. Sugimoto, M. Uemura, Org. Lett. 2001, 3, 2033-2036.
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239. T. Watanabe, Y. Tanaka, R. Shoda, R. Sakamoto, K. Kamikawa, M. Uemura, J. Org. Chem. 2004, 69, 4152-4158.
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241. b) T. Watanabe, M. Uemura, Chem. Commun. 1998, 871-872;
242. c) reference [159b].
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245. Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
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248. The synthesis of korupensamine B ((M)-137) was a formal total synthesis that ended at the enantiomer of an intermediate of the total synthesis of ent-korupensamine B (ent-(M)-137) published in the same article.
249. For an earlier atropodiastereodivergent total synthesis of korupensamines A ((P)-137) and B ((M)-137), see: G. Bringmann, M. Ochse, R. Götz, J. Org. Chem. 2000, 65, 2069-2077.
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252. T. Hattori, N. Koike, Y. Okaishi, S. Miyano, Tetrahedron Lett. 1996, 37, 2057-2060.
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270. 2 and (-)-sparteine [(-)-173] as the catalysts and AgCl as the stoichiometric cooxidant, was published in 1993; the chemical yield and optical purity, however, was low: M. Smrčina, J. Poláková, Š. Vyskočil, P. Kočovský, J. Org. Chem. 1993, 58, 4534-4538.
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273. For an earlier, less successful approach, see: a) M. Nakajima, K. Kanayama, I. Miyoshi, S. Hashimoto, Tetrahedron Lett. 1995, 36, 9519-9520;
274. b) M. Nakajima, I. Miyoshi, K. Kanayama, S. Hashimoto, N. Noji, K. Koga, J. Org. Chem. 1999, 64, 2264-2271.
275. For the oxidative coupling of 154a with up to 94% ee by using an octahydrobinaphthyl-2,2′-diamine as the ligand, see: K. H. Kim, D.-W. Lee, Y.-S. Lee, D.-H. Ko, D.-C. Ha, Tetrahedron 2004, 60, 9037-9042.
276. M. C. Kozlowski, X. Li, P. J. Carroll, Z. Xu, Organometallics 2002, 21, 4513-4522.
277. C. A. Mulrooney, X. Li, E. S. DiVirgilio, M. C. Kozlowski, J. Am. Chem. Soc. 2003, 125, 6856-6857.
278. For applications in Glaser-Hay couplings, see: X. Xie, P.-W. Phuan, M. C. Kozlowski, Angew. Chem. 2003, 115, 2218-2220;
279. Angew. Chem. Int. Ed. 2003, 42, 2168-2170.
280. R. Irie, K. Masutani, T. Katsuki, Synlett 2000, 1433-1436.
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282. Angew. Chem. Int. Ed. 2002, 41, 4532-4535;
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284. a) C.-Y. Chu, B.-J. Uang, Tetrahedron: Asymmetry 2003, 14, 53-55;
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286. c) C.-Y. Chu, D.-R. Hwang, S.-K. Wang, B.-J. Uang, Chem. Commun. 2001, 980-981:
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288. There is one additional report on an asymmetric photocatalytic oxidative hiaryl coupling with a centro- and helically chiral Ru catalyst to give (M)-binol ((M)-29) with low enantioselectivity (16% ee): T. Hamada, H. Ishida, S. Usui, Y. Watanabe, K. Tsumura, K. Ohkubo, J. Chem. Soc. Chem. Commun. 1993, 909-911.
289. T. Osa, Y. Kashiwaga, Y. Yanagisawa, J. M. Bobbit, J. Chem. Soc. Chem. Commun. 1994, 2535-2537.
290. Initial attempts by Kumada and co-workers gave only poor stereocontrol: a) K. Tamao, A. Minato, N. Miyake, T. Mastuda, Y. Kiso, M. Kumada, Chem. Lett. 1975, 133-136;
291. b) K. Tamao, H. Yamamoto, H. Matsumoto, N. Miyake, T. Hayashi, M. Kumada, Tetrahedron Lett. 1977, 18, 1389-1392.
292. T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8156.
293. PS,S)-177b to give (M)-179, was successfully performed on a large scale (up to 20 g): a) S. L. Colletti, R. L. Halterman, Tetrahedron Lett. 1989, 30, 3513-3516;
294. b) J. M. Harris, R. McDonald, J. C. Vederas, J. Chem. Soc. Perkin Trans. 1 1996, 2669-2674.
295. For less successful enantioselective Kumada cross-couplings of 175 with 176, see: a) T. Frejd, T. Klingstedt, Acta Chem. Scand. 1989, 43, 670-675;
296. b) A. Terfort, H. Brunner, J. Chem. Soc. Perkin Trans. 1 1996, 1467-1479;
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298. T. Hayashi, K. Hayashizaki, Y. Ito, Tetrahedron Lett. 1989, 30, 215-218.
299. A large portion of the "wrong" P enantiomer of the intermediate binaphthyl initially formed will ultimately, by the strong renewed external asymmetric induction again with preferential formation of M in the second step, become the meso-configured P,M compound (and not the P,P product) and thus formally further enhance the ee value of the M,M product.
300. For reviews on Suzuki cross-couplings, see: a) "Palladium-Catalyzed Aryl-Aryl Coupling" L. Anastasia, E. Negishi, in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. I (Eds. E. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 311-334;
301. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
302. a) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907-1912;
303. Angew. Chem. Int. Ed. 2004, 43, 1871-1876;
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305. c) J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163;
306. d) J. P. Wolfe, S. L. Buchwald, Angew. Chem. 1999, 111, 2570-2573;
307. Angew. Chem. Int. Ed. 1999, 38, 2413-2416:
308. e) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
309. A. N. Cammidge, K. V. L. Crépy. Chem. Commun. 2000, 1723-1724.
310. A. N. Cammidge, K. V. L. Crépy, Tetrahedron 2004, 60, 4377-4386.
311. D- value), it seems that the wrong enantiomer (P)-179 was drawn.
312. J. F. Jensen, M. Johannsen, Org. Lett. 2003, 5, 3025-3028.
313. For less atropoenantioselective Suzuki couplings with binap and derivatives thereof. see: A.-S. Castanet, F. Colobert, P.-E. Broutin, M. Obringer, Tetrahedron: Asymmetry 2002, 13, 659-665.
314. J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051-12052.
315. K. C. Nicolaou, H. Li, C. N. C. Boddy, J. M. Ramanjulu, T.-Y. Yuc, S. Natarajan, X.-J. Chu, S. Bräse, F. Rübsam, Chem. Eur. J. 1999, 5, 2584-2601.
316. For further applications in natural products synthesis. see: a) model system for (M)-rhazinilam: A. Herrbach, A. Marinetti, O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2003, 68, 4897-4905;
317. b) ancistrotanzanine B and ancistroealaine A: G. Bringmann, A. Hamm, M. Schraut, Org. Lett. 2003, 5, 2805-2808;
318. c) G. Bringmann, R.-M. Pfeifer, P. Schreiber, K. Hartner, M. Schraut, M. Breuning, Tetrahedron 2004, 60, 4349-4360.
319. [202]
320. Y. Terao, H. Wakui, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2001, 123, 10407-10408.
321. a) S. Saito, T. Kano, H. Muto, M. Nakadai, H. Yamamoto, J. Am. Chem. Soc. 1999, 121, 8943-8944;
322. b) T. Kano, Y. Ohyabu, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 2002, 124, 5365-5373.
323. The enantiomerically pure acetate of (M,M)-200 was used as the chiral auxiliary in stereoselective aldol reactions: S. Saito, K. Hatanaka, T. Kano, H. Yamamoto, Angew. Chem. 1998, 110, 3579-3582;
324. Angew. Chem. Int. Ed. 1998, 37, 3378-3381.
325. M. Shindo, K. Koga, K. Tomioka, J. Am. Chem. Soc. 1992, 114, 8732-8733.
326. For a less efficient desymmetrization of 220 via an (R)-menthone acetal, see: a) T. Harada, S. Ueda, T. Yoshida, A. Inoue, M. Takeuchi, N. Ogawa, A. Oku, M. Shiro, J. Org. Chem. 1994, 59, 7575-7576;
327. b) T. Harada, S. Ueda, T. M. T. Tuyet, A. Inoue, K. Fujita, M. Takeuchi, N. Ogawa, A. Oku, M. Shiro, Tetrahedron 1997, 53, 16663-16678.
328. For a related three-step protocol, see: a) T. Harada, T. M. T. Tuyet, K. Hashimoto, M. Hatsuda, A. Oku, Synlett 1997, 1426-1428;
329. b) T. M. T. Tuyet, T. Harada, K. Hashimoto, M. Hatsuda, A. Oku, J. Org. Chem. 2000, 65, 1335-1343.
330. T. Harada, T. M. T. Tuyet, A. Oku, Org. Lett. 2000, 2, 1319-1322.
331. a) Y.-Y. Ku, T. Grieme, P. Raje, P. Sharma, S. A. King, H. E. Morton, J. Am. Chem. Soc. 2002, 124, 4282-4286;
332. b) Y.-Y. Ku, T. Grieme, Curr. Opin. Drug Discovery Dev. 2002, 5, 852-859.
333. [212a]
334. L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss, A. H. White, J. Chem. Soc. Dalton Trans. 1988, 2403-2409.
335. T. Matsumoto, T. Konegawa, T. Nakamura, K. Suzuki, Synlett 2002, 122-124.
336. a) T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101-9102;
337. b) T. Kamikawa, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 3161-3164;
338. c) T. Kamikawa, T. Hayashi, Tetrahedron 1999, 55, 3455-3466.
339. F. Kakiuchi, P. Le Gendre, A. Yamada, H. Ohtaki, S. Murai, Tetrahedron: Asymmetry 2000, 11, 2647-2651.
340. G. Capozzi, C. Ciampi, G. Delogu, S. Menichetti, C. Nativi, J. Org. Chem. 2001, 66, 8787-8792; for the opposite approach, the intramolecular atropodiastereoselective coupling of two gallic acid units prefixed to D-glucose as a chiral tether, see references [110-112], [114].
341. K. S. Feldman, K. J. Eastman, G. Lessene, Org. Lett. 2002, 4, 3525-3528.
342. M. Penhoat, V. Levacher, G. Dupas, J. Org. Chem. 2003, 68, 9517-9520.
343. For a similar approach by Wallace and co-workers, see reference [81].
344. For a related conformational locking, see compound 37 (Figure 8).
345. a) K. Mikami, M. Yamanaka, Chem. Rev. 2003, 103, 3369-3400;
346. b) K. Mikami, K. Aikawa, Y. Yusa, J. J. Jodry, M. Yamanaka, Synlett 2002, 1561-1578.
347. a) Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, Tetrahedron Lett. 1997, 38, 2681-2684;
348. b) Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, J. Org. Chem. 2000, 65, 3326-3333.
349. For an example involving silicon as the bridging atom, see: F. Fabris, O. De Lucchi, V. Lucchini, J. Org. Chem. 1997, 62, 7156-7164.
350. 2] complex by using (P)-binol, see: a) M. D. Tudor, J. J. Becker, P. S. White, M. R. Gagné, Organometallics 2000, 19, 4376-4384;
351. b) J. J. Becker, P. S. White, M. R. Gagné, J. Am. Chem. Soc. 2001, 123, 9478-9479.
352. a) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham, R. Noyori, Angew. Chem. 1999, 111, 517-519;
353. Angew. Chem. Int. Ed. 1999, 38, 495-497;
354. b) T. Korenaga, K. Aikawa, M. Terada, S. Kawauchi, K. Mikami, Adv. Synth. Catal. 2001, 343, 284-288.
355. a) G. Bringmann, M. Breuning, P. Henschel, J. Hinrichs, Org. Synth. 2002, 79, 72-83;
356. b) reference [20a].
357. Only some selected procedures will be reported here; for more detailed information, see the original literature.
358. For an example of an atroposelective ring cleavage with an achiral hydride-transfer reagent in the presence of a chiral Lewis acid as the asymmetric inductor, see: W. A. Schenk, J. Kümmel, I. Reuther, N. Burzlaff, A. Wuzik, O. Schupp, G. Bringmann, Eur. J. Inorg. Chem. 1999, 1745-1756;
359. for the complementary approach, the coordination of an achiral Lewis acid with subsequent reduction with a chiral hydride-transfer reagent, see: G. Bringmann, A. Wuzik, J. Kümmel, W. A. Schenk, Organometallics 2001, 20, 1692-1694.
360. G. Bringmann, M. Breuning, S. Tasler, H. Endress, C. L. J. Ewers, L. Göbel, K. Peters, E.-M. Peters, Chem. Eur. J. 1999, 5, 3029-3038.
361. G. Bringmann, M. Breuning, R. Walter, A. Wuzik, K. Peters, E.-M. Peters, Eur. J. Org. Chem. 1999, 3047-3055.
362. For an atropoenantioselective ring-opening of 33c with O-nucleophiles in the presence of a chiral catalyst, see: D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, D. A. Chaplin, M. Breuning, G. Bringmann, Tetrahedron 1997, 53, 7539-7556.
363. a) G. Bringmann, T. Hartung, Angew. Chem. 1992, 104, 782-783;
364. Angew. Chem. Int. Ed. Engl. 1992, 31, 761-762;
365. b) G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1999, 10, 385-390;
366. c) G. Bringmann, T. Hartung, Synthesis 1992, 433-435;
367. d) G. Bringmann, T. Hartung, Tetrahedron 1993, 49, 7891-7902.
368. See references [20a,d].
369. The axial configuration of atropisomerically pure (P,R)-265c obtained by crystallization can be preserved by quick transformation into a configurationally stable biaryl; see reference [62].
370. H. Pellissier, Tetrahedron 2003, 59, 8291-8327.
371. rel >200!) by a "normal" (nondynamic) kinetic resolution, with subsequent recycling of the nonreacting enantiomer by thermal racemization: G. Bringmann, J. Hinrichs, J. Kraus, A. Wuzik, T. Schulz, J. Org. Chem. 2000, 65, 2517-2527.
372. G. Bringmann, S. Güssregen, D. Vitt, R. Stowasser, J. Mol. Model. 1998, 4, 165-175.
373. G. Bringmann, D. Vitt, J. Org. Chem. 1995, 60, 7674-7681.
374. For a more detailed discussion about the mechanism of the lactone reduction, including the existence of a "stereochemical leakage" at the level of the intermediates 269 and 270, see references [20a,d,e], [240].
375. [20a]).
376. For more detailed investigations on the atropoenantioselective reduction of model biaryl hydroxyaldehydes, see: a) G. Bringmann, M. Breuning, Synlett 1998, 634-636;
377. b) reference [83].
378. G. Bringmann, W. Saeb, M. Rübenacker, Tetrahedron 1999, 55, 423-432.
379. G. Bringmann, J. Hinrichs, P. Henschel, J. Kraus, K. Peters, E.-M. Peters, Eur. J. Org. Chem. 2002, 1096-1106.
380. For further kinetic resolutions of configurationally stable biaryl lactones, see: a) G. Bringmann, J. Hinrichs, Tetrahedron: Asymmetry 1997, 8, 4121-4126;
381. b) reference [238].
382. rel value of 43 was attained.
383. a) K. Kamikawa, K. Norimura, M. Furusyo, T. Uno, Y. Sato, A. Konoo, G. Bringmann, M. Uemura, Organometallics 2003, 22, 1038-1046;
384. b) K. Kamikawa, M. Furusyo, T. Uno, Y. Sato, A. Konoo, G. Bringmann, M. Uemura, Org. Lett. 2001, 3, 3667-3670.
385. a) Mastigophorene A (3): G. Bringmann, J. Hinrichs, T. Pabst, P. Henschel, K. Peters, E.-M. Peters, Synthesis 2001, 155-167
386. and G. Bringmann, T. Pabst, P. Henschel, J. Kraus, K. Peters, E.-M. Peters, D. S. Rycroft, J. Connolly, J. Am. Chem. Soc. 2000, 122, 9127-9133;
387. b) knipholone (2): reference [10b] and G. Bringmann, D. Menche, Angew. Chem. 2001, 113, 1733-1736;
388. Angew. Chem. Int. Ed. 2001, 40, 1687-1690;
389. c) korupensamine A ((P)-137): reference [165] and G. Bringmann, M. Ochse, Synlett 1998, 1294-1296;
390. d) dioncophylline C (282): G. Bringmann, J. Holenz, R. Weirich, M. Rübenacker, C. Funke, M. R. Boyd, R. J. Gulakowski, G. François, Tetrahedron 1998, 54, 497-512;
391. e) AB system 284 of vancomycin (1): G. Bringmann, D. Menche, J. Mühlbacher, M. Reichert, N. Saito, S. S. Pfeiffer, B. H. Lipshutz, Org. Lett. 2002, 4, 2833-2836.
392. (+)-Isoschizandrin (283): G. A. Molander, K. M. George, L. G. Monovich, J. Org. Chem. 2003, 68, 9533-9540.
393. (-)-Steganone ((M)-107): H. Abe, S. Takeda, T. Fujita, K. Nishioka, Y. Takeuchi, T. Harayama, Tetrahedron Lett. 2004, 45, 2327-2329.
394. a) MOP ligand 285: G. Bringmann, A. Wuzik, M. Breuning, P. Henschel, K. Peters, E.-M. Peters, Tetrahedron: Asymmetry 1999, 10, 3025-3031;
395. b) tripodal ligand 286: G. Bringmann, R.-M. Pfeifer, C. Rummey, K. Hartner, M. Breuning, J. Org. Chem. 2003, 68, 6859-6863;
396. see also: G. Bringmann, M. Breuning, R.-M. Pfeifer, P. Schreiber, Tetrahedron: Asymmetry 2003, 14, 2225-2228.
397. [212]
398. a) T. Shimada, Y-H. Cho, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 13396-13397;
399. b) Y.-H. Cho, A. Kina, T. Shimada, T. Hayashi, J. Org. Chem. 2004, 69, 3811-3823.
400. For the asymmetric Ullmann coupling to either atropisomer of 8,8′-bis(oxazolinyl)-1,1′-binaphthalene from the same oxazolidine just by applying different conditions, see: a) A. I. Meyers, A. Price, J. Org. Chem. 1998, 63, 412-413;
401. b) A. I. Meyers, M. J. McKennon, Tetrahedron Lett. 1995, 36, 5869-5872.
402. T. D. Nelson, A. I. Meyers, Tetrahedron Lett. 1993, 34, 3061-3062.
403. T. D. Nelson, A. I. Meyers, Tetrahedron Lett. 1994, 35, 3259-3262.
404. [126],[257]
405. T. D. Nelson, A. I. Meyers, J. Org. Chem. 1994, 59, 2577-2580.
406. A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121, 2762-2769; the atropodiastereomer mastigophorene B ((M)-3) was prepared accordingly.
407. In this particular case, the normally used L-valinol-derived analogue of (S)-294 gave a slightly lower selectivity (74% de).
408. For a similar reaction, see: K. Yamamoto, H. Fukushima, H. Yumioka, M. Nakazaki, Bull. Chem. Soc. Jpn. 1985, 58, 3633-3634.
409. a) Y. Zhang, S.-M. Yeung, H. Wu, D. P. Heller, C. Wu, W. D. Wulff, Org. Lett. 2003, 5, 1813-1816;
410. b) S. Yu, C. Rabalakos, W. D. Mitchell, W. D. Wulff, Org. Lett. 2005, 7, 367-369; the 7,7′-dimethyl derivative of (S)-vapol was synthesized accordingly in 78% yield with 99% ee.
411. Vanol (297) and vapol (298) were used as ligands in catalysts for asymmetric Baeyer-Villiger reactions: C. Bolm, J.-C. Frison, Y. Zhang, W. D. Wulff, Synlett 2004, 1619-1621.
412. A. Gutnov, B. Heller, C. Fischer, H.-J. Drexler, A. Spannenberg, B. Sundermann, C. Sundermann, Angew. Chem. 2004, 116, 3883-3886;
413. Angew. Chem. Int. Ed. 2004, 43, 3795-3797.
414. T. Shibata, T. Fujimoto, K. Yokota, K. Takagi, J. Am. Chem. Soc. 2004, 126, 8382-8383.
415. Y. Nishii, K. Wakasugi, K. Koga, Y. Tanabe, J. Am. Chem. Soc. 2004, 126, 5358-5359.
416. T. Hattori, M. Date, K. Sakurai, N. Morohashi, H. Kosugi, S. Miyano, Tetrahedron Lett. 2001, 42, 8035-8038.
417. For a central-to-axial chirality transfer in the field of naturally occurring biaryl compounds, see: J. M. Wanjohi, A. Yenesew, J. O. Midiwo, M. Heydenreich, M. G. Peter, M. Dreyer, M. Reichert, G. Bringmann, Tetrahedron 2005, 61, 2667-2674.
418. J. Bao, W. D. Wulff, M. J. Fumo, Eugene B. Grant, D. P. Heller, M. C. Whitcomb, S.-M. Yeung, J. Am. Chem. Soc. 1996, 118, 2166-2181.
419. A. V. Vorogushin, W. D. Wulff, H.-J. Hansen, J. Am. Chem. Soc. 2002, 124, 6512-6513.
420. J. C. Anderson, J. W. Cran, N. P. King, Tetrahedron Lett. 2003, 44, 7771-7774.