On the optimization of pig pancreatic lipase catalyzed monoacetylation of prochiral diols

Banfi, Luca; Guanti, Giuseppe; Riva, Renata

doi:10.1016/0957-4166(95)00167-n

Cited by 31 publications

(29 citation statements)

References 77 publications

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“…[14] To reduce these effects, immobilized PPL was used in the DKR studies, with Celite as solid support. [15] On the other hand, the racemization catalyzed by [{(IPr)PdBr 2 } 2 ] could not reach sufficient rate below 50 8C without prohibitive increase of catalyst loading. Therefore, at 40 8C despite the presence of the dimeric Pd complex, only ordinary kinetic resolution was obtained (Table 2, entry 1).…”

Section: Entrymentioning

confidence: 99%

Chemoenzymatic Dynamic Kinetic Resolution of Axially Chiral Allenes

Deska

Ochoa

Bäckvall

2010

Chemistry A European J

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At the palladium: Dimeric palladium bromide complexes bearing monodentate N-heterocyclic carbene ligands have been identified as efficient catalysts for the chemoselective racemization of axially chiral allenyl alcohols. In combination with porcine pancreatic lipase as biocatalyst, a dynamic kinetic resolution has been developed, giving access to optically active allenes in good yield and high enantiomeric purity (see scheme).

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Section: Entrymentioning

confidence: 99%

Chemoenzymatic Dynamic Kinetic Resolution of Axially Chiral Allenes

Deska

Ochoa

Bäckvall

2010

Chemistry A European J

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“…Although PPL is widely used for the resolution of prochiral diols, [23] we also examined other enzymes in our desymmetrisation strategy. Lipase from Candida antarctica type B (CAL B), lipase from Candida cylindracea (CCL), lipase from Pseudomonas cepacia (PCL) and from Pseudomonas fluorescens (PFL) immobilized on Sol-Gel-AK, lipase from Aspergillus niger (ANL) were tested for their activity and selectivity in the acylation reaction illustrated in Scheme 5.…”

Section: Preparation Of Enantiomerically Enriched 2-oxazolidinones Bymentioning

confidence: 99%

New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies

Neri

Williams

2003

Adv Synth Catal

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This paper describes how enantiomerically enriched Evans auxiliaries can be successfully prepared by either an enzymatic desymmetrisation strategy or an asymmetric synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N-Boc-protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4R)-and (4S)-substituted 2-oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary, by means of a diastereoselective aldol reaction coupled with a lipase-catalysed resolution, we achieved the preparation of enantiomerically enriched b-hydroxy acids and enantiomerically enriched 2-oxazolidinones.

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“…[7] [8] It is worth noting that both prochiral precursors 12 and 15 are easily available in 55% and 54% overall yield from isovaleraldehyde (Scheme 2) and that all the intermediates and final products are easily purified by distillation or crystallization. Monoacetates 19 were converted by a four step sequence into a series of asymmetrized tris(hydroxymethyl)methanes (THYM*) (21), or of asymmetrized bi(hydroxymethyl)acetaldehydes (BHYMA*) (22).…”

Section: Preparationmentioning

confidence: 99%

Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

Banfi¹,

Guanti²

1998

Eur. J. Org. Chem.

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Asymmetrized tris(hydroxymethyl)methane (THYM*) is a new chiral building block easily accessible in both enantiomeric forms by a chemoenzymatic methodology. The presence of three synthetically equivalent masked hydroxymethyl groups and a high degree of latent symmetry (C3v) makes this synthon very versatile in synthetic applications. This review describes its preparation and a series of elaborations (with particular enphasis on the diastereoselective generation of additional chiral centers) leading to advanced intermediated for the preparation of biologically active compounds.

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On the optimization of pig pancreatic lipase catalyzed monoacetylation of prochiral diols

Cited by 31 publications

References 77 publications

Chemoenzymatic Dynamic Kinetic Resolution of Axially Chiral Allenes

Chemoenzymatic Dynamic Kinetic Resolution of Axially Chiral Allenes

New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies

Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

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