Enzymatic preparation of enantiomerically pure and selectively protected 1,2- and 1,3-diols

Goergens, U.; Schneider, Manfred

doi:10.1039/c39910001066

Cited by 31 publications

(6 citation statements)

References 7 publications

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“…R′ = Et as in the case of MHBA (compare entries 1a and 2a). This observation is in agreement with the established empirical rule, which suggests that the size of the substituents is crucial for the enantioselectivity of CRL: 78,79,86,87,[94][95][96][97][98] a larger size difference between R′ and OH results in a higher enantioselectivity due to a larger difference in free energy between the transition states of the two enantiomers.…”

Section: Mechanistic Discussionsupporting

confidence: 90%

Bridging racemic lactate esters with stereoselective polylactic acid using commercial lipase catalysis

et al. 2013

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A productive and enantioselective hydrolysis of racemic mixtures of lactate esters with commercial Candida rugosa lipase was performed. This step contributes to a novel envisioned route for stereoselective PLA production by combining recent chemocatalytic developments with this biocatalytic contribution, foreseeing two separate L-and D-lactate enantiomer streams. A study of the hydrolysis kinetics identified an unexpected rate determining step at the origin of an unprecedented ester reactivity order. † Electronic supplementary information (ESI) available. See

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Section: Mechanistic Discussionsupporting

confidence: 90%

Bridging racemic lactate esters with stereoselective polylactic acid using commercial lipase catalysis

et al. 2013

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“…Furthermore, the presence of an additional heteroatom in the chiral alcohol, placed at an appropriate position from the hydroxy group, can provide further versatility to the compound. Chiral hydroxysulfides serve as important intermediates in the synthesis of naturally occurring spiroketal pheromones,45 chiral oxiranes,32,46,47 thiiranes,48 tetrahydrofurans49,50 and 4‐acetoxyazetidinones 51. Furthermore, they are readily transformed into hydroxysulfoxides52–54 or sulfones,55 which are valuable building blocks in the synthesis of natural products.…”

Section: Baker's‐yeast‐mediated Resolution Of Keto Sulfidesmentioning

confidence: 99%

Baker's‐Yeast‐Mediated Reduction of Sulfur‐Containing Compounds

Deasy

Maguire

2014

Eur J Org Chem

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Both the efficiency and the stereoselectivity in baker's‐yeast‐mediated reduction of ketones are strongly influenced by both the presence and the position of sulfur substituents, or indeed by the use of sulfur‐containing additives. Interestingly the oxidation level of the sulfur substituent has a powerful impact on the outcome of the yeast reduction. It is apparent that use of the sulfone moiety as a substituent to influence the efficiency and stereoselectivity in ketone reduction is substantially more effective than use of the analogous sulfide and sulfoxide moieties.

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“…Several methods have been proposed to preparate chiral 1,3-butanediol by microbial reduction (Ridley and Stralow 1975;Ferreira and Simonelli 1990), and lipase-catalyzed reaction (Goergens and Schneider 1991). Chemical syntheses of chiral 1,3-butane-diol have also been reported (Gerlach et al 1976;Murakami et al 1980;Hintzer et al 1982;Tai et al 1983;Takano et al 1983;Harada et al 1987;Hoffmann et al 1987;Kitamura et al 1988;Kitamura et al 1991).…”

Section: Introductionmentioning

confidence: 99%