γ-Syn-selective carbonyl allylation by 1-bromo-2-butene with tin(II) iodide and tetrabutylammonium bromide

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7103-7106

  Masuyama, Yoshiro ^a   Kishida, Masayuki ^a   Kurusu, Yasuhiko ^a  

^a SOPHIA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ALLYL COMPOUND;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01584-5     Document Type: Article

References (17)

1. 1. For a review, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
2. 2. (a) Masuyama, Y. J. Synth. Org. Chem., Jpn. 1992, 50, 202-212;
3. (b) Masuyama, Y. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1994; Vol. 3, pp. 255-303.
4. 3. Masuyama, Y.; Kishida, M.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1995, 1405-1406.
5. 4. For carbonyl allylation by allylic bromides with tin(II) chloride or bromide, see: (a) Gambaro, A.; Peruzzo, V.; Plazzogna, G.: Tagliavini, G. J. Organomet. Chem. 1980, 197, 45-50;
6. (b) Mukaiyama, T.; Harada, T.; Shoda, S. Chem. Lett. 1980, 1507-1510.
7. 5. For carbonyl allylation by allylic bromides with tin, see: (a) Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 1527-1528;
8. (b) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191-193.
9. 6. 1-Bromo-2-butene (1; X=Br, E:Z=85:15), which has been purchased from Tokyo Chemical Industry Co., Ltd., contains 14% 3-bromo-1-butene [(E)-1:(Z)-1:3-bromo-1-butene=ca.73:13:14]. (E)-1-Chloro-2-butene (1; X=Cl) was also purchased from Tokyo Chemical Industry Co., Ltd.
10. 7. Masuyama, Y.; Nakata, J.; Ktirusu, Y. J. Chem. Soc., Perkin Trans. 1 1991, 2598-2599.
11. 5, 0.13 g, 78 %, syn:anti=84:16) as a colorless oil.
12. 5, 115 h, 22%, syn:anti=40:60) and tin(II) iodide has not functioned. Thus, allylic alcohols are probably impractical in the carbonyl allylation with tin(II) bromide or iodide.
13. 13 (equation presented)
14. 11. Tin(IV) compounds, prepared in the initial stage by the hydrolysis of products, 2-methyl-3-butenyloxybromodiiodotins or 2-methyl-3-butenyloxydibromodiiodostannate, may function as Lewis acids in the reaction of 2-butenylbromodiiodorin or 2-butenyldibromodiiodostannate, which is hard to form six-membered cyclic transition states.
15. 12. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577-2586.
16. 13. Pentacoordination of aromatic diolate or fluoride to silicon or tin of allylic silanes and tins usually promotes carbonyl allylations to lead to γ-anti-selection via six-membered cyclic transition states: (a) Sakurai, H. Synlett 1989, 1-8:
17. (b) Denmark, S. E.: Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163. and references cited therein.