An asymmetric synthesis of MK-0417. Observations on oxazaborolidine-catalyzed reductions

Jones, Todd K.; Mohan, Julie J.; Xavier, Lyndon C.; Blacklock, Thomas J.; Mathre, David J.; Sohár, Pàl; Jones, E. Tracy Turner; Reamer, Robert A.; Roberts, F. E.; Grabowski, Edward J. J.

doi:10.1021/jo00002a050

Cited by 158 publications

(50 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…210 The oxazaborolidine catalyzed borane reduction was chosen for the high yield (99%) since yeast gave the opposite selectivity and (Ipc) 2 BCl made for difficult separations. The catalytic reduction was optimized with (S)-MeCBS for kilogram scale production of chiral alcohol 366, and (S)-DPP was recovered in 95% yield (Scheme 137).…”

Section: Enantioselective Ketone Reductionmentioning

confidence: 99%

Boron Reagents in Process Chemistry: Excellent Tools for Selective Reductions

2006

View full text Add to dashboard Cite

Section: Enantioselective Ketone Reductionmentioning

confidence: 99%

Boron Reagents in Process Chemistry: Excellent Tools for Selective Reductions

2006

View full text Add to dashboard Cite

“…The enantiomeric excesses of alcohols 5, 18 and 25 were determined by the preparation of the diastercomeric Mosher esters using R-( + )-cc-methoxy-( trifluoromethy])-phenylacetic acid chloride (Mosher acid chloride) and were found to be 99% [20]. The enantiomeric excess values of the subsequent chiral materials were assumed to be 99%.…”

Section: Generulmentioning

confidence: 99%

An investigation into the effect of lateral fluoro substitution in the molecular core on the spontaneous polarization of chiral cyclohexanes

et al. 1996

View full text Add to dashboard Cite

“…Optically pure building blocks are in continuous demand for the construction of more selective drugs in medicinal chemistry [10][11][12] or in aromas chemistry [13,14] as compared to any chemical process for preparation of chiral secondary alcohols, lipase-catalyzed kinetic resolution is more viable and easy to scale up on industrial level. Particularly, heterocyclic compounds are common fragments found in several natural and unnatural bioactive compounds [15]. Herein, we present studies on the resolution of heteroaryl alcohols used for the preparation of a small library of enantiomerically pure building blocks in a green fashion.…”

Section: Introductionmentioning

confidence: 99%

Easy preparation of enantiomerically enriched heteroaromatic alcohols through lipase-catalyzed acylation with succinic anhydride under unconventional activation

Melais

Boukachabia

Aribi‐Zouioueche

et al. 2015

Bioprocess Biosyst Eng

View full text Add to dashboard Cite

This study reports the lipase-catalyzed resolution of heteroaromatic secondary alcohols by succinic anhydride under different activation conditions by convenient procedure with succinic anhydride. The effects of succinic anhydride and the nature of the heteroatom are discussed in standard conditions in the kinetic resolution with lipases. The results recorded under microwave activation and ultrasonication is compared. (R)-4-chromanol was obtained in optically pure form (ee > 99%) with a high selectivity E > 200 by Pseudomonas cepacia lipase (PCL) in diethyl ether, using microwave radiation and under ultrasonication. The reaction time is reduced compared to the conventional heating with a better control of the selectivity of the lipase PCL. A significant effect of the nature of the heteroatoms on the reactivity and selectivity of the lipase with succinic anhydride has been disclosed, regardless the conditions of activation. This method proved to be clean, fast, interesting alternative, and facilitates the use of a cyclic anhydride, by microwave or ultrasound especially with secondary alcohols. The process is a valuable prerequisite for the preparative scale production of enantiomerically heteroaromatic alcohols in sustainable chemistry.

show abstract

An asymmetric synthesis of MK-0417. Observations on oxazaborolidine-catalyzed reductions

Cited by 158 publications

References 0 publications

Boron Reagents in Process Chemistry: Excellent Tools for Selective Reductions

Boron Reagents in Process Chemistry: Excellent Tools for Selective Reductions

An investigation into the effect of lateral fluoro substitution in the molecular core on the spontaneous polarization of chiral cyclohexanes

Easy preparation of enantiomerically enriched heteroaromatic alcohols through lipase-catalyzed acylation with succinic anhydride under unconventional activation

Contact Info

Product

Resources

About