Kinetic Resolution of Racemic Secondary Alcohols Catalyzed by Chiral Diaminodiphosphine−Ir(I) Complexes

Li, Yanyun; Zhang, Xueqin; Dong, Zhen‐Rong; Shen, Weiyi; Chen, Gui; Gao, Jingxiang

doi:10.1021/ol062244f

Cited by 64 publications

(21 citation statements)

References 25 publications

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“…In 2006, Gao et al. reported that chiral diaminodiphosphine‐Ir(I) complexes of 36 efficiently catalyzed the KR of secondary arylalkanols with excellent enantioselectivities of up to 98% ee under mild conditions 83. In the presence of a base such as KOH in acetone, the process allowed selectivity factors of up to 34 to be reached (Scheme ).…”

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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Section: Kinetic Resolution Of Alcoholsmentioning

confidence: 99%

Catalytic Non‐Enzymatic Kinetic Resolution

Pellissier

2011

Adv Synth Catal

326

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“…[17][18][19][20][21] Recently, researchers have developed several effective non-enzymatic catalysts for the oxidative kinetic resolution (OKR) of racemic alcohols. [22][23][24][25] In the last two decades, different chiral ligands with palladium, [26][27][28][29][30][31][32] ruthenium, [33][34][35] iridium, 36,37 cobalt, 38 iron, 39 and manganese (Mn) metal ions have been used as catalysts for OKR of racemic secondary alcohols. In particular, chiral Mn(III) salen complexes are considered to be the most effective catalyst for the OKR of racemic secondary alcohols ( Figure 1) because of their facile synthesis and catalytic reaction condition with high turnover frequency.…”

Section: Introductionmentioning

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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“…Among the many processes known, the oxidative kinetic resolution (OKR) of racemic secondary alcohols is a particularly attractive and efficient method [12][13][14][15]. Several chiral complexes pre-prepared or generated in situ from the corresponding chiral ligands with Pd [16][17][18][19][20][21][22], Ru [23][24][25], Ir [26][27][28], Co [29], Fe [30], and Mn [31][32][33][34][35][36][37][38][39] ions have been used as catalysts for the OKR of racemic secondary alcohols. Among these metal complexes, chiral Mn(III)-salen complexes [31][32][33][34][35][36][37] are of special interest due to their easy synthesis, mild reaction conditions and very short reaction time.…”

Section: Introductionmentioning

confidence: 99%