Diastereoselective radical cyclization of chiral β-alkoxyacrylates

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7765-7768

  Lee, Eun ^a   Jeong, Jin Wook ^a   Yu, Yunjae ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ALCOHOL; LACTONE;

ARTICLE; CHIRALITY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030721612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10074-0     Document Type: Article

References (16)

1. a) Lee, E.; Tae, J. S.; Lee, C.; Park, C. M. Tetrahedron Lett. 1993, 34, 4831-4834.
2. b) Lee, E.; Tae, J. S.; Chong, Y. H.; Park, Y. C.; Yun, M.; Kim, S. Tetrahedron Lett. 1994, 35, 129-132.
3. c) Lee, E.; Park, C. M. J. Chem. Soc. Chem. Comm. 1994, 293-294.
4. d) Lee, E.; Park, C. M.; Yun, J. S. J. Am. Chem. Soc. 1995, 117, 8017-8018.
5. e) Lee, E. Pure & Appl. Chem. 1996, 68, 631-634.
6. f) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31-34.
7. g) Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252-2253.
8. h) Evans, P. A.; Roseman, J. D.; Garber, L. T. J. Org. Chem. 1996, 61, 4880-4881.
9. a) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455-6456.
10. b) Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269-272.
11. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asym. 1995, 6, 2657-2660.
12. Nishida, M.; Hayashi, H.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Synlett 1995, 1045-1046.
13. The 3-bromopropoxy, 4-bromobutoxy, and 3-butynoxy derivatives gave cyclization products without any stereoselection under the high temperature/high dilution conditions. The reaction of the 3-bromopropoxy derivative yielded less than 5 % d.e. of the tetrahydrofuranyl product at 0 °C in the presence of excess boron trifluoride etherate.
14. For discussions of NMR correlation studies, see: Lee, E.; Lee, Y. R.; Moon, B.; Kwon, O.; Shim, M. S.; Yun, J. S. J. Org. Chem. 1994, 59, 1444-1456.
15. Huang, D.-L.; Draper, R. W. Tetrahedron Lett. 1994, 35, 661-662.
16. (2R,3S)-3-Phenylcholestan-2-ol and propiolic acid reacted in the presence of DCC and a catalytic amount of DMAP in ether to give 80 % yield of the propiolate. It was reacted with 1,4-dihydroxybutane in the presence of 0.5 equivalent of tributylphosphane in dichloromethane, and 71 % yield of the 4-hydroxybutoxy derivative was obtained, which was oxidized with PCC to give 92 % yield of 4.