A stereocomplementary approach to β-lactones: Highly diastereoselective synthesis of cis-β-lactones, a β-chloro acid, and a tetrahydrofuran

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1197-1199

  Wang, Yingcai ^a   Zhao, Cunxiang ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003433635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990860o     Document Type: Article

References (29)

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3. (c) Lowe, C.; Vederas, J. C. Org. Prep. Proc. Int. 1995, 27, 305-346.
4. (d) Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403-6434. For some related and complementary methods for the stereoselective synthesis of β-lactones, see:
5. (e) Danheiser, R. L.; Nowick, J. S.; Lee, J. H.; Miller, R. F.; Huboux, A. H. Org. Synth. 1996, 73, 61-72.
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13. Zhao, C.; Romo, D., manuscript submitted.
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19. The cleavage of β-lactones to β-chloro and β-bromo carboxylic acids is known, see: (a) Pu, Y.; Martin, F. M.; Vederas, J. C. J. Org. Chem. 1991, 56, 1280-1283.
20. (b) Labrouillere, M.; Le Roux, C.; Oussaid, A.; Gaspard-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1995, 132, 522-530.
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22. Use of the TES - ketene acetal 2b leads to greater amounts of β-lactone at the expense of β-chloro silyl ester. This is consistent with competitive attack of chloride ion at the β-carbon rather than silicon since a bulkier silyl group should divert attack to the β-carbon.
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24. (a) Mikami, K.; Shimizu, M. Tetrahedron 1996, 52, 7287-7296.
25. (b) See ref 8a.
26. For some approaches to β-chloro carboxylic acids, see: (a) Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J. J. Org. Chem. 1994, 59, 2238-2240 and references cited.
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28. (c) Also see ref 10.
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