Modification of chiral dimethyl tartrate through transesterification: Immobilization on POSS and enantioselectivity reversal in sharpless asymmetric epoxidation

Chirality

Volumn 22, Issue 7, 2010, Pages 675-683

  García, Rafael A ^a   Van Grieken, Rafael ^a   Iglesias, José ^a   Sherrington, David C ^b   Gibson, Colin L ^b  

^a UNIVERSIDAD REY JUAN CARLOS   (Spain)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Asymmetric epoxidation; Enantioselectivity reversal; POSS; Tartrate ligands; Transesterification

Indexed keywords

ALLYL ALCOHOL; DIMETHYL TARTRATE; LIGAND; TARTARIC ACID; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; EPOXIDATION; ESTERIFICATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 77952755854     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20814     Document Type: Article

References (28)

1. Katsuki T, Sharpless KB. The first practical method for asymmetric epoxidation. J Am Chem Soc 1980;102:5974-5976.
2. Martin VS, Woodard SS, Katsuki T, Yamada Y, Ikeda M, Sharpless KB. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity? J Am Chem Soc 1981;103:6237-6240.
3. Hanson RM, Sharpless KB. Procedure for the catalytic asymmetric epoxidation of allylic alcohols in the presence of molecular sieves. J Org Chem 1986;51:1922-1925.
4. Gao Y, Sharpless KB. Asymmetric synthesis of both enantiomers of Tomoxetine and Fluoxetine. Selective reduction of 2,3-Epoxycinnamyl alcohol with Red-Al. J Org Chem 1988;53:4081-4084.
5. Katsuki T, Martin VS. Organic reactions. New York: Wiley; 1996. p 1-299.
6. Canali L, Karjalainen JK, Sherrington DC, Hormi O. Efficient polymer-supported sharpless alkene epoxidation catalyst. Chem Commun 1997;123-124. (Pubitemid 127496939)
7. Meunier D, Piechaczyk A, De Mallmann A, Basset JM. Silica supported tantalum catalysts for asymmetric epoxidations of allylic alcohols. Angew Chem Int Ed 1999;38:3540-3542.
8. Xiang S, Zhang Y, Xin Q, Li C. Asymmetric epoxidation of allylic alcohol on organic-inorganic hybrid chiral catalysts grafted onto the surface of silica and in the mesopores of MCM-41. Angew Chem Int Ed Engl 2002;41:821-824.
9. Zhao W, Hao ZP, Hu C, Li J, Xu X. The epoxidation of allylic alcohol on Ti-complex/MCM-48 catalysts. Microporous Mesoporous Mater 2008;112:133-137. (Pubitemid 351657443)
10. 2(tmeda)] on silica and comparison with its reaction with a silsesquioxane. Chem Eur J 2005;11:7358-7365.
11. Mintcheva N, Tanabe M, Osakada K. Preparation and structure of new phenylplatinum complexes containing silsesquioxane as a monodentate or bidentate ligand. Organometallics 2006;25:3776-3783. (Pubitemid 44116006)
12. Pérez Y, Pérez Quintanilla D, Fajardo M, Sierra I, Del Hierro I. Immobilization of titanium chiral alkoxides on SBA-15 and modelling the active sites of heterogeneous catalyst using titanium silsesquioxane complexes. J Mol Catal A 2007;271:227-237. (Pubitemid 46710514)
13. Kawasaki T, Ishikawa K, Sekibata H, Sato I, Soai K. Enantioselective synthesis induced by chiral organic-inorganic hybrid silsesquioxane in conjunction with asymmetric autocatalysis. Tetrahedron Lett 2004; 45:7939-7941. (Pubitemid 39296500)
14. Ionescu G, Van Der Vlugt JI, Abbenhuis HCL, Vogt D. Synthesis and applications of chiral phosphite ligands derived from incompletely condensed silsesquioxane backbones. Tetrahedron Asymmetry 2005;16:3970-3975. (Pubitemid 41773075)
15. Gao Y, Hanson RM, Klunder JM, Ko Soo Y, Masamune H, Sharpless KB. Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization. J Am Chem Soc 1987;109:5765-5780.
16. Barlow JS, Dixon DJ, Foster AC, Ley SV, Reynolds DJ. New building blocks for efficient and highly diastereoselective polyol production - synthesis and utility of (R0,R0,S,S) and (S0,S0,R,R)-2,3-butane diacetal protected butane tetrol derivatives. J Chem Soc Perkin Trans 1 1999;12:1627-1630.
17. Seebach D. Modern synthetic methods. Frankfurt/Main: Wiley; 1980. p 113-171.
18. Dixon DJ, Foster AC, Ley SV, Reynolds DJ. Preparation of desymmetrised meso-tartrate derivatives - synthesis and utility of (R′,R′,S,R)-2, 3-butane diacetal procected butane tetrol. J Chem Soc Perkin Trans 1 1999;12:1631-1633.
19. Uri A, Tuulmets A, Palm V. Transesterification of esters of carboxylic acids by titanium-alcoholates 2. Transesterification of esters of aromatic acids. Org Rectivity (Tartu) 1983;20:122-131.
20. Furlán RLE, Mata EG, Mascaretti OA. Butylstannonic acid catalyzed transesterification of carboxylic esters. Tetrahedron Lett 1998;39:2257-2260.
21. Kociensky PJ. Protecting groups. Sttutgart: Thieme; 1994. p 96-102.
22. Shimizu I, Matsumoto Y, Shoji K, Ono T, Satake A, Yamamoto A. Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio. Tetrahedron Lett 1996;37:7115-7118.
23. Altava B, Berruguete MI, Fraile JM, Garcia JI, Luis SV, Mayoral JA, Vicent MJ. How important is the inner matrix of supported enantiomeric catalysts? Reversal of topicity with two polystyrene backbones. Angew Chem Int Ed 2000;39:1503-1506.
24. Trost BM, Fettes A, Shireman BT. Direct catalytic asymmetric aldol additions of methyl ynones. Spontaenous reversal in the sense of enantioinduction. J Am Chem Soc 2004;126:2660-2661.
25. Arseniyadis S, Valleix A, Wagner A, Miokowski C. Kinetic resolution of amines: a highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity. Angew Chem Int Ed 2004;43:3314-3317.
26. Altava B, Berruguete MI, Garcia-Verdugo E, Luis SV, Vicent MJ. Functional monolytic resins for the development of enantioselective versatile catalytic minireactors with long-term stability: TADDOL supported systems. Green Chem 2006;8:717-726.
27. Reed NN, Dickerson TJ, Boldt GE, Janda KD. Enantioreversal in the Sharpless asymmetric epoxidation reaction controlled by the molecular weight of a covalently appended achiral polymer. J Org Chem 2005;70:1728-1731.
28. Lutz F, Igarashi T, Kawasaki T, Soai K. Small amounts of chiral b-amino alcohols reverse the enantioselectivity of chiral catalysts in cooperative asymmetric autocatalysis. J Am Chem Soc 2005;127:12206-12207.