Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen–Mn(III) complexes

Fu-rong, Han; Zhao, Jiquan; Zhang, Yuecheng; Wang, Weiyu; Zuo, Yi; An, Jingkun

doi:10.1016/j.carres.2008.04.022

Cited by 15 publications

(3 citation statements)

References 29 publications

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“…The solvent generally plays a critical role in the OKR of secondary alcohols [33,43,44]. Thus, it was important to study the effect of the solvent on the OKR of secondary alcohols in this system.…”

Section: Resultsmentioning

confidence: 99%

Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System

et al. 2014

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Section: Resultsmentioning

confidence: 99%

Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System

et al. 2014

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“…Enantioselectivities of up to 89% ee have been reported by Han et al. for the KR of 1‐phenylethanol using novel chiral Mn(salen) complexes with sugar moieties in comparable conditions 86. However, the catalyst stability, product and catalyst separation of this process remained difficult.…”

Section: Kinetic Resolution Of Alcoholsmentioning

confidence: 99%

Catalytic Non‐Enzymatic Kinetic Resolution

Pellissier

2011

Adv Synth Catal

326

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While tremendous advances have been made in asymmetric synthesis, the resolution of racemates is still the most important industrial approach to the synthesis of chiral compounds. The use of enzymes for the kinetic resolution (KR) of racemic substrates to afford enantiopure compounds in high enantioselectivity and good yield has long been a popular strategy in synthesis. However, transition metal-mediated and more recently organocatalyzed KRs have gained popularity within the synthetic community over the last two decades due to the progress made in the development of chiral catalysts for asymmetric reactions. Many catalytic non-enzymatic procedures have been developed providing high enantioselectivity and yield for both products and recovered starting materials. Indeed, the non-enzymatic KR of racemic compounds based on the use of a chiral catalyst is presently an area of great importance in asymmetric organic synthesis. The goal of this review is to provide an update on the principal developments of catalytic non-enzymatic KR covering the literature since 2004. This review is subdivided into seven sections, according to the different types of compounds that have been resolved through catalytic non-enzymatic KR, such as alcohols,

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“…Considering the significance of sugar‐based chiral Mn(III) salen complexes in the asymmetric epoxidation of unfunctional olefins, F. Han et al in 2008 explored the catalytic applicability of Mn(III) salen complexes with sugar moieties at C‐5(5′) of the salicylaldehyde on OKR of racemic secondary alcohols . The synthesized chiral catalysts showed good results for the OKR of 1‐phenylethanol using PhI(OAc) 2 as an oxidant.…”

Section: Chiral Mn(iii) Salen Complexes For Okr Of Racemic Secondary mentioning

confidence: 99%

Advances in asymmetric oxidative kinetic resolution of racemic secondary alcohols catalyzed by chiral Mn(III) salen complexes

2017

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Enantiomerically pure secondary alcohols are essential compounds in organic synthesis and are used as chiral auxiliaries and synthetic intermediates in the pharmaceutical, agrochemical, and fine chemical industries. One of the attractive and practical approaches to achieving optically pure secondary alcohols is oxidative kinetic resolution of racemic secondary alcohols using chiral Mn(III) salen complexes. In the last decade, several chiral Mn(III) salen complexes have been reported with excellent enantioselectivity and activity in the homogeneous and heterogeneous catalysis of the oxidative kinetic resolution of racemic secondary alcohols. This review article is an overview of the literature on the recent development of chiral Mn(III) salen complexes for oxidative kinetic resolution of racemic secondary alcohols. The catalytic activity of monomeric, dimeric, macrocyclic, polymeric, and silica/resin supported chiral Mn(III) salen complexes is discussed in detail.

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Oxidative kinetic resolution of 1-phenylethanol catalyzed by sugar-based salen–Mn(III) complexes

Cited by 15 publications

References 29 publications

Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System

Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System

Catalytic Non‐Enzymatic Kinetic Resolution

Advances in asymmetric oxidative kinetic resolution of racemic secondary alcohols catalyzed by chiral Mn(III) salen complexes

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