Highly stereoselective intramolecular Michael addition using α-sulfinyl vinyllithium as an unprecedented Michael donor

Organic Letters

Volumn 3, Issue 1, 2001, Pages 29-31

  Maezaki, Naoyoshi ^a   Yuyama, Sachiko ^a   Sawamoto, Hiroaki ^a   Suzuki, Tomoko ^a   Izumi, Mayuko ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

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ARTICLE;

EID: 0042868732     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006697a     Document Type: Article

References (28)

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7. Haynes, R. K.; Katsifis, A. G. Aust. J. Chem. 1989, 42, 1473-1483. Haynes, R. K.; Katsifis, A. G. J. Chem. Soc., Chem. Commun. 1987, 340-342.
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10. Selected references, see: Jeyaraj, D. A.; Kapoor, K. K.; Yadav, V. K.; Gauniyal, H. M.; Parvez, M. J. Org. Chem. 1998, 63, 287-294. Ihara, M.; Suzuki, S.; Taniguchi, N.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1993, 2251-2258.
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15. Selective synthesis of (E)- and (Z)-1 is also possible; see: ref 3a and Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
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19. (a) Posner, G. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 2A, pp 225-241.
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23. The esters (2Z,6E)-2b-d were selectively synthesized from (E)-1 by a procedure similar to that for 2a except that Ando's protocol (Ando, K. J. Org. Chem. 1999, 64, 8406-8408) was used for construction of the (Z)-enoate moiety.
24. The substrates (2E,7E)- and (2Z,7E)-2e were synthesized by a procedure similar to that for 2a using 5-(tetrahydro-2H-pyran-2-yloxy)-pentanal as a starting material.
25. Yabuuchi, T.; Kusumi, T. J. Org. Chem. 2000, 65, 397-404.
26. D +84.4)].
27. The compound 10 was used as a starting material of (+)-hirsutic acid (Nishida, M.; Iseki, K.; Shibasaki, M.; Ikegami, S. Chem. Pharm. Bull. 1991, 38, 3230-3237) and chaulmoogric acid (Mislow, K.; Steinberg, I. V. J. Am. Chem. Soc. 1955, 77, 3807-3810).
28. The compound 10 was used as a starting material of (+)-hirsutic acid (Nishida, M.; Iseki, K.; Shibasaki, M.; Ikegami, S. Chem. Pharm. Bull. 1991, 38, 3230-3237) and chaulmoogric acid (Mislow, K.; Steinberg, I. V. J. Am. Chem. Soc. 1955, 77, 3807-3810).