Virtually complete enantioface differentiation in carbonyl group reduction by a complex aluminum hydride reagent

Noyori, Ryoji; Tomino, I.; Tanimoto, Yoshifumi

doi:10.1021/ja00505a056

Cited by 262 publications

(80 citation statements)

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“…15 -19 The synthetic routes of the brominated derivatives of AMB are also shown in Scheme 1. (2). To acetic anhydride (1.21) was added a-toluidine (214 g, 2 mol) with stirring at 50°C.…”

Section: Axially Dissymmetric Biphenyl Diaminesmentioning

confidence: 99%

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Kanoh

Goka

Murose

et al. 1987

Polym J

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ABSTRACT:Enantiomer-selective polymerization of (RS)-IX-methylbenzyl methacrylate [(RS)-MBMA] was investigated in toluene at -30oc. Reaction products between cyclohexylmagnesium bromide (cHexMgBr) and axially dissymmetric 2,2 '-diamino-6,6' -dimethylbiphenyl (AMB) in the mole ratio of 1.5: I were used as a chiral initiating system. The polymer produced a biphenyl group from the catalyst fragment. The polymerization proceeded in an anionic coordination mechanism and the racemic monomer was kinetically resolved during the course of the reaction. The enantiomer selectivity ratio when using (R)-AMB was estimated to be r

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“…15 -19 The synthetic routes of the brominated derivatives of AMB are also shown in Scheme 1. (2). To acetic anhydride (1.21) was added a-toluidine (214 g, 2 mol) with stirring at 50°C.…”

Section: Axially Dissymmetric Biphenyl Diaminesmentioning

confidence: 99%

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Kanoh

Goka

Murose

et al. 1987

Polym J

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“…reduction of ketones with LiAlH 4 in 1979, [4] which opened the gates for axially chiral biaryls as chiral ligands, auxiliaries, and organocatalysts in asymmetric reactions. As a result, numerous C 2 -symmetric, axially chiral BINOL and BI-NAP analogs and other binaphthyl derivatives have been synthesized and tested as chiral ligands or catalysts in a variety of organic transformations.…”

Section: Introductionmentioning

confidence: 99%

Ar‐BINMOLs with Axial and sp³Central Chirality – Characterization, Chiroptical Properties, and Application in Asymmetric Catalysis

et al. 2011

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Abstract2′‐Hydroxy‐1,1′‐binaphthalene‐2‐(arylmethanol) (Ar‐BINMOLs), a family of new 1,1′‐binaphthalene‐2,2′‐diol derivatives, prepared by a [1,2]‐Wittig rearrangement, are introduced as new chiral molecules for the study of the modes of supramolecular aggregation on the basis of ESI‐MS, NMR spectroscopy, differential scanning calorimetry (DSC), and X‐ray diffractometry. Characterization showed that Ar‐BINMOLs exhibit different characteristics to BINOL and act as supramolecules due to hydrogen bonding and aromatic π–π/C–H···π interactions. In particular, CD measurements of chiral and racemic Ar‐BINMOL 2a in solution and the solid state show a strong Cotton effect, which revealed that amplification of chirality was observed because of the formation of a chiral supramolecular oligomer derived from the racemic monomer. To this end, the Ar‐BINMOLs were used as supramolecular auxiliaries to mediate the Michael reaction of anthrone to (E)‐β‐nitrostyrene and could give the Michael adduct with comparable enantioselectivities. In addition, the Ar‐BINMOLs act as ligands to promote asymmetric 1,2‐addition of diethylzinc to aldehydes, which resulted in excellent yields and enantioselectivities (up to >99.9 % ee) in the reactions of diethylzinc with a broad range of aromatic aldehdyes.

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“…84) The formate ester 78, which is epimeric at C3Ј, thus obtained underwent basic hydrolysis and then MnO 2 oxidation to form the a,b-conjugated ketone 79. (S)-BINAL-H reduc- tion 85) provided the (3ЈS)-alcohol 80 (97% de), which then underwent hydrogenation over PtO 2 followed by removal of the Boc protecting group. The resultant amino alcohol 81 was subjected to cyclodehydration using CBr 4 and PPh 3 13) to give the tricyclic amine 82 with complete inversion of the configuration at C-3Ј.…”

Section: Synthesis Of (؊)-Lepadiforminementioning

confidence: 99%

Development of New Synthetic Methods and Its Application to Total Synthesis of Nitrogen-Containing Bioactive Natural Products

Kibayashi

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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A group of naturally occurring substances containing nitrogen is widely distributed in plants as well as in fungi, animal, marine organisms, and insects, and many exhibit significant biological activity. These natural products with a huge variety of chemical structures include antibiotics, antitumor agents, immunostimulants, drugs affecting the cardiovascular and central nervous systems, analgesics etc. The diverse activities and low natural abundance of this group of natural products when coupled with their molecular complexity warrant development of new and efficient synthetic methods and strategy for the total synthesis of these products, in particular alkaloids. The purpose of this review is to describe some of our achievements in the total synthesis of the naturally-occurring bases including the Dendrobatid alkaloids pumiliotoxin B and allopumiliotoxin A, the anitibiotic streptazolin, the tricyclic marine alkaloids isolated from the ascidians such as fasicularin, lepadiformine, and cylindricine C, and the dimeric monoterpene alkaloid incarvillateine as well as the formal total synthesis of the spirocyclic marine alkaloids halichlorine and pinnaic acid, which are isolated from the Japanese marine sponge and the Okinawan bivalve, respectively.

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Virtually complete enantioface differentiation in carbonyl group reduction by a complex aluminum hydride reagent

Cited by 262 publications

References 0 publications

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Ar‐BINMOLs with Axial and sp³Central Chirality – Characterization, Chiroptical Properties, and Application in Asymmetric Catalysis

Development of New Synthetic Methods and Its Application to Total Synthesis of Nitrogen-Containing Bioactive Natural Products

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Virtually complete enantioface differentiation in carbonyl group reduction by a complex aluminum hydride reagent

Cited by 262 publications

References 0 publications

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Highly Asymmetric-selective and Stereoselective Polymerization of (RS)-α-Methylbenzyl Methacrylate with Cyclohexyl-magnesium Bromide-Axially Dissymmetric 2,2′-Diamino-6,6′-dimethylbiphenyl System

Ar‐BINMOLs with Axial and sp3Central Chirality – Characterization, Chiroptical Properties, and Application in Asymmetric Catalysis

Development of New Synthetic Methods and Its Application to Total Synthesis of Nitrogen-Containing Bioactive Natural Products

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Ar‐BINMOLs with Axial and sp³Central Chirality – Characterization, Chiroptical Properties, and Application in Asymmetric Catalysis