3-Bromopenta-2,4-dienylsilane: A useful reagent for the preparation of [3]dendralenes and polycyclic compounds

Molecular Diversity

Volumn 17, Issue 1, 2013, Pages 49-53

  Rahif, Mohammed ^a   Roux, Maryline ^a   Thibonnet, Jérôme ^b   Parrain, Jean Luc ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

^b UNIVERSITÉ DE TOURS   (France)

Author keywords

Bromopentadienylsilane; Dendralenes; Diversity; Heterocycles; Polycycles; Tandem cycloaddition

Indexed keywords

1 TRIMETHYLSILYL 3 BROMOPENTA 2,4 DIENE; [3]DENDRALENE; CARBONYL DERIVATIVE; POLYCYCLIC HYDROCARBON; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONJUGATION; CYCLOADDITION; DIELS ALDER REACTION; ELIMINATION REACTION; POLYMERIZATION; PRIORITY JOURNAL;

CATALYSIS; POLYCYCLIC COMPOUNDS; TRIMETHYLSILYL COMPOUNDS;

EID: 84873398391     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-012-9418-6     Document Type: Article

References (24)

1. Masse CE, Panek JS (1995) Diastereoselective reactions of chiral allyl and allenyl silanes with activated C:Xpi-bonds. Chem Rev 95:1293-1316. doi: 10.1021/cr00037a008
2. McLaughlin MG, Cook MJ (2012) Domino alkene-isomerization-Claisen rearrangement strategy to substituted allylsilanes. J Org Chem 77:2058-2063. doi: 10.1021/jo202560g
3. Hanhan NV, Ball-Jones NR, Ngon NT, Annaliese KF (2012) Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: synthesis of spirooxindoles. Angew Chem Int Ed 51:989-992. doi: 10.1002/anie.201105739
4. Chabaud L, James P, Landais Y (2004) Allylsilanes in organic synthesis - recent developments. Eur J Org Chem 2004:3173-3199. doi: 10.1002/ejoc.200300789 (references cited therein)
5. Lahrech M, Hacini S, Parrain J-L, Santelli M (1997) A general synthesis of β -silylallenes from allylsilanes. Tetrahedron Lett 38:3395-3398. doi: 10.1016/S0040-4039(97)00628-X
6. Roux M, Santelli M, Parrain J-L (2000) 3-Bromopentadienylsilane: a new reagent for the introduction of a functional pentadienyl unit with fixed configuration. Org Lett 2:1701-1704. doi: 10.1021/ol0058137
7. Hopf H (2000) Classics in hydrocarbon chemistry: syntheses concepts perspectives. Wiley-VCH, Weinheim
8. Hopf H (2009) Nature 460:183-184. doi: 10.1038/460183a
9. Trahanovsky WS, Koeplinger KA (1992) Synthesis and dimerization of two cross-conjugated trienes: 3-methylene-1,4-pentadiene and 1,2,3- trimethylenecyclohexane. J Org Chem 57:4711-4716. doi: 10.1021/jo00043a032
10. Payne AD, Bojase G, Paddon-Row MN, Sherburn MS (2009) Practical synthesis of the dendralene family reveals alternation in behavior. Angew Chem Int Ed 48:4836-4839. doi: 10.1002/anie.200901733
11. Woo S, Squires N, Fallis AG (1999) Indium-mediated γ- pentadienylation of aldehydes and ketones: cross-conjugated trienes for diene-transmissive cycloadditions. Org Lett 1:573-576. doi: 10.1021/ol990695c
12. Woo S, Legoupy S, Parra S, Fallis AG (1999) A diene transmissive Diels-Alder strategy for oxygenated nor-steroid and triterpenoid skeletons. Org Lett 1:1013-1016. doi: 10.1021/ol990798v
13. Kwon O, Park SB, Schreiber SL (2002) Skeletal diversity via a branched pathway: efficient synthesis of 29,400 discrete, polycyclic compounds and their arraying into stock solutions. J Am Chem Soc 124:13402-13404. doi: 10.1021/ja028086e
14. Fielder S, Rowan DD, Sherburn MS (2000) First synthesis of the dendralene family of fundamental hydrocarbons. Angew Chem Int Ed 39:4331-4333. doi: 10.1002/1521-3773(20001201)39:23<4331:AID-ANIE4331>3.0.CO;2-3
15. Brummond KM, You L (2005) Consecutive Rh(I)-catalyzed Alder-ene/Diels-Alder/Diels-Alder reaction sequence affording rapid entry to polycyclic compounds. Tetrahedron 61:6180-6185. doi: 10.1016/j.tet.2005.03.141
16. Martin H-D, Eckert-Maksić M, Mayer B (1980) Diagonal interaction in the four-membered ring. Experimental demonstration of a dominating circumannular conjugation: 5,6-dimethylenebicyclo[2.1.1]hexane. Angew Chem Int Ed Engl 19:807-809. doi: 10.1002/anie.198008071
17. Le Nôtre J, Martinez AA, Dixneuf PH, Bruneau C (2003) Synthesis of new terpene derivatives via ruthenium catalysis: rearrangement of silylated enynes derived from terpenoids. Tetrahedron 59: 9425-9432. doi: 10.1016/j.tet.2003.09.073
18. E 2′ chirality transfer reactions. Eur J Org Chem 2012:1656-1663. doi: 10.1002/ejoc.201101634
19. Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H (1986) Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis. J Am Chem Soc 108:6048-6050. doi: 10.1021/ja00279a068
20. Brown PA, Jenkin PR (1982) Tetrahedron Lett 23:3733-3734. doi: 10.1016/S0040-4039(00)88670-0
21. Wada E, Kanemassa S, Fujiwara I, Tsuge O (1985) A new facile synthesis of 2-substituted 1,3-butadiene derivatives via palladium-catalyzed cross-coupling reaction of 2,3-alkadienyl carbonates with organoboron compounds. Bull Chem Soc Jpn 58:1942-1945. doi: 10.1246/bcsj.58.1942
22. Kulinkovich OG, Sviridov SV, Vasilevski DA (1991) Generation and reactions of low-valent titanium alkoxide-acetylene complexes. A practical preparation of allyl alcohols. Synthesis 234. doi: 10.1055/s-1991-26431
23. Okamoto S, Sato H, Sato F (1996) Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes. Tetrahedron Lett 37:8865-8868. doi: 10.1016/S0040-4039(96)02126-0
24. Winkler JD (1996) Tandem Diels-Alder cycloadditions in organic synthesis. Chem Rev 96:167-176. doi: 10.1021/cr950029z