High Regio-, Chemo-, and stereoselectivity via low-temperature 4 + 3 cycloadditions. Convergent synthesis of multifunctionalized vinylmetals (M = Si, Sn) and S-vinyl benzenecarbothioates

Organic Letters

Volumn 2, Issue 7, 2000, Pages 883-886

  Beck, Hartmut ^a,b   Stark, Christian B W ^a   Hoffmann, H Martin R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000792432     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991386p     Document Type: Article

References (41)

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31. 2-Substituted furans react with high regioselectivity: Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. Murray, D. H.; Albizati, K. F. Tetrahedron Lett. 1990, 31, 4109.
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34. (b) 3-Stannylfurans were synthesized according to Bailey, T. R. Synthesis 1991, 242.
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36. The chiral auxiliaries remain configurationally stable under the reaction conditions (ref 11c). Products are obtained as single isomers (ee > 98%). See also: X-ray crystal structure of cycloadducts 11A, 11B, and 13A (Table 1).
37. -1. (1S,2R,5S)-Benzenecarbothioic Acid, S-[4-Methyl-3-oxo-2-{(1R)-phenylethoxy}-8-oxabicyclo[3.2.1]oct-6-en-6-yl] Ester (13 A).
38. Hoffmann, H. M. R. Angew. Chem. 1984, 96, 29; Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
39. Hoffmann, H. M. R. Angew. Chem. 1984, 96, 29; Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
40. In our model the tether of allyl cation and aryl group facilitates π-stacking and thus enhances selectivity. Replacement of the methyl group (box) by a simple hydrogen generates a more floppy ensemble of reactants and causes not only loss of stereoselection as expected (racemic mixture of cycloadducts) but also collapse of regioselectivity (anti:syn = 1.1:1)!
41. 3,4-Dibromofuran was synthesized according to: Gorzynski, M.; Rewicki, D. Liebigs Ann. Chem. 1986, 625.