Highly diastereoselective hydrogenations leading to β-hydroxy δ-lactones in hydroxy-protected form. A modified view of δ-lactone conformations

Journal of the American Chemical Society

Volumn 125, Issue 39, 2003, Pages 11942-11955

  Brandänge, Svante ^a   Färnbäck, Magnus ^a   Leijonmarck, Hans ^a   Sundin, Anders ^b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; HYDROGENATION; SUBSTRATES; X RAY CRYSTALLOGRAPHY;

SKEW CONFORMATIONS;

STEREOCHEMISTRY;

1 OXA 3 CYCLOHEXEN 2 ONE; ACETIC ACID; BETA HYDROXY DELTA LACTONE; CARBON; DELTA LACTONE; DELTA VALEROLACTONE; HYDROXYL GROUP; LACTONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CATALYSIS; CONFORMATION; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; HYDROGENATION; MOLECULAR MECHANICS; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HYDROGENATION; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0141508976     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036002b     Document Type: Article

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159. (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp 686 and 1199.
160. (b) Ibid., pp 698 and 706.
161. (c) Ibid., p 688.
162. (d) Ibid., p 619.
163. (e) Ibid., pp 688-689 and 1210.
164. Eliel, E. L.; Manoharan, M. J. Org. Chem. 1981, 46, 1959-1962.
165. (a) Seebach, D.; Chow, H.-F.; Jackson, R. F. W.; Sutter, M. A.; Thaisrivongs, S.; Zimmerman, J. Liebigs Ann. Chem. 1986, 1281-1308.
166. (b) Fukui, M.; Okamoto, S.; Sano, T.; Nakata, T.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 2890-2892.
167. (c) Nakata, T.; Komatsu, T.; Nagasawa, K.; Yamada, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 8225-8228.
168. (d) Tholander, J.; Carreira, E. M. Helv. Chim. Acta 2001, 84, 613-622.
169. (a) Corey, E. J.; Gras, J.-L.; Ulrich, P. Tetrahedron Lett. 1976, 17, 809-812.
170. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley: New York, 1999; pp 41-44.
171. Anet, F. A. L.; Chmurny, G. N.; Krane, J. J. Am. Chem. Soc. 1973, 95, 4423-4424.
172. Langley, C. H.; Lii, J.-H.; Allinger, N. L. J. Comput. Chem. 2001, 22, 1451-1475.
173. We found this TS which probably is the lowest barrier.
174. Anet, F. A. L.; Freedberg, D. I.; Storer, J. W.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 10969-10971.
175. (a) Prugh, J. D.; Deana, A. A. Tetrahedron Lett. 1988, 29, 37-40.
176. (b) Bravo, P.; Resnati, G.; Viani, F.; Arnone, A. Tetrahedron 1987, 43, 4635-4647.
177. (c) Pasquet, G.; Boucherot, D.; Pilgrim, W. R. Tetrahedron Lett. 1980, 21, 931-934.
178. (d) Kefurt, K.; Snatzke, G.; Snatzke, F.; Trska, P.; Jary, J. Collect. Czech. Chem. Commun. 1974, 41, 3324-3334.