Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

Zhou, Ling; Tay, Daniel Weiliang; Chen, Jie; Leung, Gulice Y. C.; Yeung, Ying‐Yeung

doi:10.1039/c2cc36578b

Cited by 79 publications

(31 citation statements)

References 64 publications

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“…Procedure for the Synthesis of Allylic Alcohols 17a and 17f: 11b A solution of the appropriate diene (0.2 mmol) and silver trifluoroacetate (1.1 equiv., 0.22 mmol) in acetone/water (3:1; 2.0 mL) was stirred at 50 °C for 20 h with light exclusion. After this time, brine (2.0 mL) was added, and the mixture was filtered through Celite and washed with ethyl acetate.…”

Section: Methodsmentioning

confidence: 99%

Intramolecular Bromoamination of Conjugated N‐Tosylaminodienes Using N‐Bromosuccinimide. Synthesis of Bromoallyl‐Substituted N‐Heterocycles and Their Applications as Building Blocks

et al. 2013

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The bromonium-promoted cyclization of conjugated aminodienes is described. The reaction proceeds smoothly in the presence of N-bromosuccinimide as halonium promoter, and using N-tosyl-protected aminodienes as substrates, to give the corresponding halocyclization products in high yields and with high diastereoselectivities. It can be envisaged that the formation of these products is the result of an S N 2Ј-type ring-opening of a terminal bromonium intermediate in a 5-4962 exo-trig or 6-exo-trig cyclization mode. The presence of an allyl bromide moiety in the haloamination products makes these molecules highly attractive from a synthetic point of view, as it opens the way for further transformations. Thus, allylic substitution reactions with different nucleophiles (acetate, azide, cyanide, and malonate), palladium-catalysed Suzuki coupling, and silver-mediated bromine displacement reactions were carried out successfully.General Procedure for the Bromoamination of Dienes: A solution of the aminodiene (0.2 mmol) in dry dichloromethane (0.7 mL) was added dropwise to a solution of N-bromosuccinimide (1.2 equiv., 0.24 mmol) in the same solvent (0.3 mL) under an argon atmosphere. The reaction mixture was stirred for 12 h at room temperature. After this time, the reaction was quenched by the addition of NaHCO 3 (saturated aq.; 2 mL). The organic phase was separated, and the aqueous phase was extracted with CH 2 Cl 2 (2 ϫ 3 mL). The combined organic extracts were dried (MgSO 4 ) and concentrated. The residue was purified by flash chromatography using hexane/ www.eurjoc.org

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Section: Methodsmentioning

confidence: 99%

Intramolecular Bromoamination of Conjugated N‐Tosylaminodienes Using N‐Bromosuccinimide. Synthesis of Bromoallyl‐Substituted N‐Heterocycles and Their Applications as Building Blocks

et al. 2013

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“…It is worth noting that enantioselective haloaminocyclizations of alkenes could deliver the chiral vicinal amino halide products which are versatile synthetic intermediates, have been received considerable scientific attention. A series of catalysis systems have been developed, such as chiral Lewis bases,– Lewis acids,– chiral amines, as well as chiral phosphoric acids –. Specifically, the chiral thiourea‐based catalysts and Cu(II)‐complex have achieved great progress in the haloaminocyclization approaches to chiral indolines.…”

Section: Figurementioning

confidence: 99%

Enantioselective Synthesis of 2‐Bromomethyl Indolines via BINAP(S)‐Catalyzed Bromoaminocyclization of Allyl Aniline

Deng

2017

Adv Synth Catal

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“…In addition to constructing the pyrrolidine system, piperidine is also a class of synthetically useful molecule. With a similar approach, we successfully converted trans ‐1,2‐disubstituted olefinic amide 67 into 2‐substituted 3‐bromopiperidine 68 with the quinine‐derived thiocarbamate catalyst 69 (Scheme ) . The yields and ee values of the desired piperidines 68 are generally high.…”

Section: Thiocarbamate and Carbamate Catalystsmentioning

confidence: 99%

Lewis Base Catalyzed Stereo‐ and Regioselective Bromocyclization

Gieuw

Yeung

2016

The Chemical Record

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Oxygen- and nitrogen-containing heterocyclic compounds are widely recognized as key components in many natural products and biologically relevant molecules, but often the problem comes down to methodologies in synthesizing them. Halocyclization of olefinic substrates is a promising strategy in the construction of O- and N-heterocyclic compounds, which further signifies the development of their asymmetric variants. Over the past years, our group has been devoted to this particular area of asymmetric electrophilic halocyclization with chalcogen-containing molecules as catalysts. In this account, the main focus is on the development of our novel chiral catalysts and applications derived from the reaction products.

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Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process

Cited by 79 publications

References 64 publications

Intramolecular Bromoamination of Conjugated N‐Tosylaminodienes Using N‐Bromosuccinimide. Synthesis of Bromoallyl‐Substituted N‐Heterocycles and Their Applications as Building Blocks

Intramolecular Bromoamination of Conjugated N‐Tosylaminodienes Using N‐Bromosuccinimide. Synthesis of Bromoallyl‐Substituted N‐Heterocycles and Their Applications as Building Blocks

Enantioselective Synthesis of 2‐Bromomethyl Indolines via BINAP(S)‐Catalyzed Bromoaminocyclization of Allyl Aniline

Lewis Base Catalyzed Stereo‐ and Regioselective Bromocyclization

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