A new synthesis of α-arylglycines from aryl boronic acids

Petasis, Nicos A.; Goodman, Andrew; Zavialov, Ilia A.

doi:10.1016/s0040-4020(97)01028-4

Cited by 208 publications

(73 citation statements)

References 39 publications

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“…3). [96][97][98][99][100] Although studies on asymmetric induction have achieved some remarkable success, particularly in diastereoselective processes using chiral ahydroxyaldehydes, [101][102][103][104] there are no reports on catalytic enantioselective processes using chiral catalysts. On the basis of this mechanism, we designed a new thiourea bearing a 1,2-amino alcohol, which can coordinate to organoboronic acids.…”

Section: Chiral Multifunctional Thioureas With Coordinating Abilitymentioning

confidence: 99%

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

2010

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We have developed several multifunctional thiourea catalysts bearing a tertiary amine or an 1,2-amino alcohol in expectation of their synchronous activation of a nucleophile and an electrophile through both acid-base and hydrogen-bonding interactions. From these studies, it was revealed that the weak acidity of thioureas compared with metallic Lewis acids could be overcome by this modification. The bifunctional aminothiourea could be used efficiently for a wide range of diastereoselective and enantioselective nucleophilic reactions such as Michael addition of 1,3-dicarbonyl compounds to nitroolefines, aza-Henry reaction of nitroalkanes to N-Boc imines, and hydrazination of cyclic b b-keto esters. We also discovered that multifunctional thiourea catalyst, bearing an 1,2-amino alcohol moiety, significantly accelerated the Petasis-type reaction of alkenylboronic acids to Nphenoxycarbonyl quinolinium salts, prepared from quinolines and phenyl chloroformate, to afford 1,2-addition products with high enantioselectivity (up to 97% ee). Furthermore, to expand the synthetic applicability of the thiourea-catalyzed asymmetric reactions, tandem organocatalyzed reactions were explored to establish the concise one-pot synthesis of chiral densely functionalized three-, five-, and six-membered compounds.

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Section: Chiral Multifunctional Thioureas With Coordinating Abilitymentioning

confidence: 99%

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

2010

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“…Unfortunately no addition product was formed ( Table 2, entry 2). In view of the strong Lewis acidity of cationic Pd(II) complexes, [12] PdA C H T U N G T R E N N U N G (CF 3 CO 2 ) 2 was used instead of the AlCl 3 and PdA C H T U N G T R E N N U N G (OAc) 2 , but the same result was obtained (Table 2, entry 3). When the combination of PdA C H T U N G T R E N N U N G (CF 3 CO 2 ) 2 and ligand 9 was used, a satisfactory result (65 % yield and 76 % ee) was obtained ( Table 2, entry 4).…”

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confidence: 70%

“…[1] The synthesis of optically active arylglycines has received much attention [1,2] and the application of asymmetric catalysis towards the formation of these compounds is a fundamental challenge. [3,4] Ellman reported a diastereoselective synthesis of arylglycine derivatives by the rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinylimino esters, [5] which proceeds in high yields with very high diastereoselectivity for both electron-rich and electron-poor arylboronic acids. Recently, we reported a similar work using cationic palladium catalysis.…”

mentioning

confidence: 99%

Palladium(II)‐Catalyzed One‐Pot Enantioselective Synthesis of Arylglycine Derivatives from Ethyl Glyoxylate, p‐Toluenesulfonyl Isocyanate and Arylboronic Acids

Dai

Yang

2008

Adv Synth Catal

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“…Radical addition to glyoxylic oxime ethers is not only a very promising approach to the synthesis of aliphatic a-amino acids but also complements the nucleophilic addition of organometallic reagents. [41][42][43] We found that electron-deficient N-sulfonylimines 30 exhibit excellent reactivity toward nucleophilic alkyl radicals even in the absence of strong Lewis acids.…”

Section: Reactivity Of Imine Derivativesmentioning

confidence: 99%

Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application

Naito

2008

Chem. Pharm. Bull.

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Nitrogen-containing compounds are core parts not only of natural and synthetic medicines but also of biologically active compounds including natural products. This review focuses on the development of new synthetic reactions for nitrogen-containing compounds via three methodologies: the reductive photocycloaddition reaction of enamides, radical addition reaction, and nucleophilic addition reaction. Newly developed reactions were successfully applied to the synthesis of various types of nitrogen-containing compounds including medicines, lead compounds to new drugs, natural alkaloids, and others.

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A new synthesis of α-arylglycines from aryl boronic acids

Cited by 208 publications

References 39 publications

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

Palladium(II)‐Catalyzed One‐Pot Enantioselective Synthesis of Arylglycine Derivatives from Ethyl Glyoxylate, p‐Toluenesulfonyl Isocyanate and Arylboronic Acids

Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application

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