Stereoselection in radical cyclization of β-alkoxyvinyl sulfoxides: Synthesis of tetrahydrofuranyl allyl carbinols

Organic Letters

Volumn 6, Issue 12, 2004, Pages 1895-1897

  Keum, Gyochang ^a   Kang, Soon Bang ^b   Kim, Youseung ^b   Lee, Eun ^a  

^a Seoul National University   (South Korea)

^b Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ALKOXYVINYL SULFOXIDE; METHANOL DERIVATIVE; SULFOXIDE; TETRAHYDROFURANYL CARBINOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 3042833041     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049676f     Document Type: Article

References (6)

1. Annonaceous acetogenins are representative examples. See, for example: Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306.
2. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366-368.
3. For references, see: Lee, E. In Radicals in Organic Synthesis, Vol. 2: Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; pp 303-333.
4. Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
5. 4 was used as a Lewis acid in chelation-controlled Sakurai reaction: Koert, U.; Stein, M.; Wagner, H. Liebigs Ann. 1995, 1415-1426. In our case, it may be important to realize that there are three oxygen atoms per molecule for coordination.
6. Use of magnesium bromide for chelation-controlled allyl transfer reaction for a α-benzyloxyaldehyde was reported: Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265-268.