“It hurts my head to think about it” - SMEs and the Legal Framework for International Commercial Contracts

The exercise of party autonomy through careful contractual drafting allows parties contracting across borders to stipulate the applicable law and dispute resolution process most appropriate to the transaction at hand. This paper reflects on empirical and legal research to consider the perceptions and experiences of small businesses in New Zealand in relation to the legal framework for international commercial contracts. The inclusion of choice of law and dispute resolution provisions can greatly increase certainty in relation to the applicable legal framework. However, the introduction of more suitable default positions for international transactions is warranted to more adequately meet the needs of New Zealand’s SMEs and provide more meaningful access to justice

“It hurts my head to think about it” - SMEs and the Legal Framework for International Commercial Contracts

The exercise of party autonomy through careful contractual drafting allows parties contracting across borders to stipulate the applicable law and dispute resolution process most appropriate to the transaction at hand. This paper reflects on empirical and legal research to consider the perceptions and experiences of small businesses in New Zealand in relation to the legal framework for international commercial contracts. The inclusion of choice of law and dispute resolution provisions can greatly increase certainty in relation to the applicable legal framework. However, the introduction of more suitable default positions for international transactions is warranted to more adequately meet the needs of New Zealand’s SMEs and provide more meaningful access to justice

Palladium Catalyzed Stereospecific Allylic Substitution of 5-Acetoxy-2(5H)-furanone and 6-Acetoxy-2H-pyran-3(6H)-one by Alcohols

Enantiomerically pure 5-acetoxy-2(5H)-furanone and 6-acetoxy-2H-pyran-3(6H)-one are converted into 5-alkoxy-2(5H)-furanones and 6-alkoxy-2H-pyran-3(6H)-ones by a palladium catalyzed allylic substitution. The reactions proceed with nearly complete retention of configuration, resulting in products with ee’s of 95%.

Lipase Catalyzed Enantioselective Transesterification of 5-Acyloxy-2(5H)-Furanones

Several lipases catalyse the transesterification of γ-acyloxyfuranones in organic solvents with high enantioselectivities. This method has been used for the kinetic resolution of 5-acetoxy-2(5H)-furanone, 5-acetoxy-4-methyl-2(5H)-furanone and 5-propionyloxy-2(5H)-furanone, in e.e.’s ranging from 68-98%.

Lipase-Catalyzed Second-Order Asymmetric Transformations as Resolution and Synthesis Strategies for Chiral 5-(Acyloxy)-2(5H)-furanone and Pyrrolinone Synthons

By use of lipase R (Amano, Penicillium roqueforti) immobilized on Hyflo Super Cell it is possible to convert at ambient temperature 5-hydroxy-5H-furan-2-one (5) to acetic acid 5-oxo-2,5-dihydrofuran-2-yl ester (1b) by acylation with vinyl acetate in 1:1 cyclohexane-butyl acetate. At 90% conversion the enantiomeric excess of 1b is 100%. This is an example of an enzyme-catalyzed second-order transformation whereby the unreactive enantiomer of 5 racemizes during reaction, allowing up to 100% conversion and obtainment of high enantiomeric excesses. The method is even more effective with 5-(acyloxy)-2(5H)-pyrrolinones. Racemic acetic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester (2) when treated with the lipase from Candida antarctica at ambient temperature in 3:1 n-hexane-butanol undergoes exactly 50% conversion to afford (+)-2 in >99% enantiomeric excess. This is the unreactive enantiomer. The (-)-enantiomer is converted to the 5-hydroxy derivative 6, which with Candida antarctica in 1:1 n-hexane-vinyl acetate at 69 °C (the temperature is higher to increase the rate of racemization) is transformed (100% conversion) to (-)-2, obtained in >99% enantiomeric excess. The scope of these second-order asymmetric transformations is discussed as well as procedures for optimalization of reaction conditions whereby transesterification strategies are combined with those of second-order asymmetric transformation.