Transformation of aldehydes into (E)-1-alkenylboronic esters with a geminal dichromium reagent derived from a dichloromethylboronic ester and CrCl

Synlett

Volumn 1995, Issue 9, 1995, Pages 963-964

  Takai, Kazuhiko ^a,b   Shinomiya, Norio ^a,b   Kaihara, Hiroya ^a,b   Yoshida, Naomi ^a,b   Moriwake, Toshio ^a,b   Utimoto, Kiitiro ^a,b  

^a OKAYAMA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

chromium(II); E 1 alkenylboronic ester; geminal dichromium reagent

Indexed keywords

EID: 0001782661     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5141     Document Type: Article

References (26)

1. Brown, H. C.; Bhat, N. G.; Somayaji, V. Organometallics 1983, 2, 1311. For the synthesis of (Z)-l-alkeny!boronic esters, see
2. Brown, H. C.; Imai, T. Organometallics 1984, 3, 1392.
3. Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951.
4. Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett. 1987, 28, 1443.
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9. Wuts, P. G. M.; Thompson, P. A. J. Organomet. Chem. 1982, 234, 137.
10. Chromium(II) chloride (99% purity) was purchased from Aldrich Chemical Co.
11. The E/Z selectivity was determined by GLPC and 1/8NMR.
12. Nakatsukasa, S.; Takai, K.; Utimoto, K. J. Org. Chem. 1986, 51, 5045.
13. Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
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16. Miyano, S.; Hida, M.; Hashimoto, H. J. Organomet. Chem. 1968, 12, 263.
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20. Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573.
21. Similar low geometrical selectivity of the produced olefin was observed in iodomethylenation of cyclohexylideneacetaldehyde with the reagent derived from CHI3 and CrCl2
22. Takai, K.; Utimoto, K. J. Synth. Org. Chem., Jpn. 1988, 46, 66
23. Saccomano, N. A. In Comprehensive Organic Synthesis, Vol. 1; Trost B. M., Ed; Pergamon Press: Oxford, 1991; p 173
24. Cintas, P. Synthesis 1992, 248.
25. Compound 6: IR (neat): 2985, 2935, 2855, 1718, 1640, 1360, 1310, 1000, 975, 850 cm'1; 1/8NMR (CDCI3): 6 1.15-1.46 (m, 22H), 1.46-1.63 (m, 2H), 2.06-2.20 (m, 2H), 2.12 (s, 3H), 2.40 (t, J= 6.8 Hz, 2H), 5.40 (d, J= 18.0 Hz, 1H), 6.61 (dt, J= 18.0, 6.5 Hz, 1H).
26. An alcohol derived by hydrolysis of the intermediate 7 was not observed by TLC throughout the reaction.