Paterson aldol reaction

The so-generated ester serves at the same time as a protecting group and renders the Evans-Tishchenko reaction a transformation in natural product syntheses. Scheme 2.146 shows a typical combination of Paterson aldol reaction followed by anti-selective reduction. The DlPCl-mediated aldol reaction sets the configuration at the new secondary alcohol (102). This configuration is then used for the... 

SCHEME 8.16. The Paterson aldol reaction using a chiral Z-enolate. 

Bernard A, A M CapeUi, A Comotti, C Gannari, J M Goodman and I Paterson 1990. Transltion-St Modeling of the Aldol Reaction of Boron Enolates A Force Field Approach. Journal of Orga Chemistry 55 3576-3581. 

Paterson, I., Florence, G.J., Gerlach, K., Scott, J.P., Sereinig, N. (2001) A Practical Synthesis of (-F)-Discodermolide and Analogues Fragment Union by Complex Aldol Reactions. Journal of the American Chemical Society, 123, 9535-9544. 

The synthesis of the BC-ring fragment 26 begins with the enantioselective aldol reaction of aldehyde 22 and chiral boron enolate 23 derived from (—)-DIP-Cl as described by Paterson and Brown [42]. The aldol adduct 24 is converted to the... 

Scheme 22 Vinylogous aldol reaction used in Paterson s synthesis of swinholide A...

C. J. Cowden, I. Paterson, Asymmetric Aldol Reactions Using Boron Enolates, Org. Prep. Proced. Int. 

I. Paterson C. J. Cowden, D. J. Wallace, Stereoselektive Aldol Reactions in the Synthesis of Polyketide Natural Products, in Modem Carbonyl Chemistry, Ed. J. Otera, Wiley-VCH, Weinheim, 2000, 249-297. 

The most direct method for the preparation of polyol frameworks is without doubt the aldol reaction. The diastereofacial selectivity of the reaction can be controlled by /J-alkoxy groups in both the methylketone enolate and the aldehyde. As investigations by Evans [6] and Paterson [7] and their groups have demonstrated, the correct selection of enolization conditions and the protective group for the )8-hydroxy group are important for the stereocontrol of the reaction. 

For a comprehensive review, see Paterson, I. The Aldol Reaction Transition Metal Enolates ,... 

In the enantioselective total synthesis of p-lactone enzyme inhibitor (-)-ebelactone A and B, I. Paterson and coworkers constructed seven stereocenters and a trisubstituted alkene plus a very sensitive p-lactone ring. The backbone of their strategy applied an aldol reaction / Ireland-Claisen rearrangement sequence and used minimal functional group manipulation. The Ireland-Claisen rearrangement was performed in the presence of an unprotected ketone moiety and set a precedent for this protocol. The diastereoselectivity was 96 4, indicating highly ( )-selective silylketene acetal formation. 

Paterson, I. The Aldol Reaction Transition Metal Enolates. in Comp. Org. Synth, (eds. Trost, B. M.,Fleming, I.), 1, 301-319 (Pergamon Press, Oxford, 1991). 

Bernard , A., Gennari, 0., Goodman, J. M., Paterson, I. The rational design and systematic analysis of asymmetric aldol reactions using... 

Cowden, C. J., Paterson, I. Asymmetric aldol reactions using boron enolates. Org. React. 1997, 51, 1-200. 

Paterson, I., Doughty, V. A., Florence, G., Gerlach, K., McLeod, M. D., Scott, J. P., Trieselmann, T. Asymmetric aldol reactions using boron enolates applications to polyketide synthesis. ACS Symp. Ser. 2001, 783, 195-206. 

Gennari, C., Hewkin, C. T., Molinari, F., Bemardi, A., Comotti, A., Goodman, J. M., Paterson, I. The rational design of highly stereoselective boron enolates using transition-state computer modeling a novel, asymmetric anti aldol reaction for ketones. J. Org. Chem. 1992, 57, 5173-5177. 

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