Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

Li, Peihe; Ma, Nuannuan; Wang, Zheng; Dai, Qipu; Hu, Changwen

doi:10.1021/acs.joc.8b00970

Cited by 9 publications

(8 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[3] tert-Butyl aminocarbonate was synthesized as reported. [9,10] Synthesis of azanyl esters: [11][12][13] To a solution of carboxylic acid (1 equiv), tert-butyl aminocarbonate [10,11] (1.2 equiv), and 4-dimethylaminopyridine (DMAP) (10 mol %) in dichloromethane (0.2 M) at 0 °C was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (1.2 equiv.) in one portion.…”

Section: Methodsmentioning

confidence: 99%

“…HPLC analysis for determining the ee value: Daicel Chiralpak IG column, 250 × 4.6 mm, mobile phase nhexane/iPrOH 9 : 1 (v/v) with 0.1 % TFA, flow rate 1.0 mL/min, UV detection at 210 nm, 25 °C; t 1 = 10.8 min, t 2 = 16.2 min. (12). [3] Synthesized from tert-butyl (2-(4-chlorophenyl)acetoxy)carbamate (57.2 mg, 0.2 mmol) using 2 mol % (R,R)-FeBIP.…”

Section: (S)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)aceticmentioning

confidence: 99%

See 1 more Smart Citation

N‐Boc‐Protected α‐Amino Acids by 1,3‐Migratory Nitrene C(sp³)−H Insertion

Meggers

2023

Eur J Org Chem

View full text Add to dashboard Cite

N‐Boc‐protected α‐amino acids are synthesized in two steps from linear or branched carboxylic acid feedstocks. In the first step, the carboxylic acid is coupled with tert‐butyl aminocarbonate (BocNHOH) to generate azanyl ester (acyloxycarbamate) RCO2NHBoc. In the second step, this azanyl ester undergoes a stereocontrolled iron‐catalyzed 1,3‐nitrogen migration to generate the N‐Boc‐protected non‐racemic α‐amino acid. This straightforward protocol is applicable to the catalytic asymmetric synthesis of α‐monosubstituted α‐amino acids with aryl, alkenyl, and alkyl side chains. Furthermore, α,α‐disubstituted α‐amino acids are accessible in an enantioconvergent fashion from racemic carboxylic acids. The new method is also advantageous for the synthesis of α‐deuterated α‐amino acids. N‐Boc‐protected α‐amino acids synthesized using this two‐step protocol are ready‐to‐use building blocks.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: (S)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)aceticmentioning

confidence: 99%

N‐Boc‐Protected α‐Amino Acids by 1,3‐Migratory Nitrene C(sp³)−H Insertion

Meggers

2023

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…图式 32 锰催化酰胺脱氧反应 Scheme 32 Manganese catalyzed deoxygenation of amide 汞催化 [97] 的脱羧反应、钛催化 [98] 的脱羟基化反应、钙介导 [99] 的炔醇脱羟基化反应以及以碳酸铯作碱 [100] 的分子内脱羧反应陆续得以发展.…”

Section: 银催化的去官能团化反应unclassified

Recent Advances in Transition-Metal Catalyzed Defunctionalization Reaction

Dong¹,

Jin²,

Liu³

2020

Chin. J. Org. Chem.

View full text Add to dashboard Cite

Functional groups are atoms or groups that determine the chemical properties of organic compounds. It often plays the role of guiding group in organic synthesis chemistry. Defunctionalization is the chemical transformation of a substrate with more functional groups into a compound with fewer functional groups, which has positive applications in solving environmental problems, resource shortage and biomass degradation. But due to the bond energy, heating, acid or base are often involved in defunctionalization. In recent years, defunctionalization has been moving toward a greener and more sustainable direction. Metal catalysis provides a new way for defunctionalization. The recent applications of different metalmediated defunctionalization in organic synthesis and their mechanism are summarized.

show abstract

“…Early studies focused on in-situ converting alkyl boronates to more electrophilic alkylboron compounds prior to amination. In this aspect, H. C. Brown et al, 8 J. M. Brown et al, 9 Matteson et al, 10 and Aggarwal et al 5a have done important contributions. In 2012, the Morken group pioneered an elegant protocol for the direct amination of alkyl pinacol boronates by using freshly prepared free methoxylamine (H2N-OMe) as the reagent (Scheme 1a).…”

mentioning

confidence: 99%