Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

Arai, Heihachiro; Sugaya, Naomi; Sasaki, Neri; Makino, Kazuishi; Lectard, Sylvain; Hamada, Y.

doi:10.1016/j.tetlet.2009.02.095

Cited by 73 publications

(40 citation statements)

References 39 publications

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“…[27] This process was promoted by the catalyst 65 in the presence of NaOAc or Na 2 CO 3 additives, yielding Boc-protected 2-formylazirines 66 in high to excellent stereoselectivities (Scheme 20).…”

Section: Domino Reactions Initiated By An Aza-michael Additionmentioning

confidence: 99%

Organocatalytic Asymmetric Aza‐Michael Additions

Enders

Wang

Liebich

2009

Chemistry A European J

448

147

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The catalytic aza-Michael addition is an important reaction within synthetic organic chemistry, given the significance of the biologically and synthetically interesting products, such as beta-amino acids and beta-lactams. In the last decade organocatalysis emerged as a powerful tool in asymmetric synthesis and had a large impact on the development of asymmetric and catalytic conjugate additions of nitrogen nucleophiles to Michael acceptors. In this review a first summary of the recent rapid progress of asymmetric organocatalyzed aza-Michael reactions is presented.

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Section: Domino Reactions Initiated By An Aza-michael Additionmentioning

confidence: 99%

Organocatalytic Asymmetric Aza‐Michael Additions

Enders

Wang

Liebich

2009

Chemistry A European J

448

147

View full text Add to dashboard Cite

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“…These reaction conditions were also applied 8 to cyclohexenone and β-methyl cyclohexenone, leading to the corresponding aziridine with 98 and 73 % ee, respectively. (Table 1, compare entries 1 and 3 with 2 and 4) [20], but in this case, the presence of a base was mandatory to obtain the corresponding 2-formylaziridines 16. This catalyst was also used for the aziridination of aromatic α,β-unsaturated aldehydes.…”

Section: Methodsmentioning

confidence: 99%

“…Other aromatic aldehydes bearing electron-withdrawing groups were also suitable substrates to yield products 16 in high yield and enantioselectivity ( Table 1, entry 8). Further oxidation transformations of products 16 allowed the synthesis of chiral β-amino esters derivatives [19,20]. …”

Section: N-4-mentioning

confidence: 99%

Recent Advances on the Organocatalyzed Enantioselective α-heterofunctionalization of Carbonyl Compounds

Guillena¹,

Ramón

2011

COC

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Abstract:This review covers literature on organocatalyzed enantioselective α-heterofunctionalization of carbonyl compounds from 2006 to 2009. In this review, we will consider those reactions in which a new carbon-heteroatom bond is formed using a chiral organic molecule as catalyst, excluding those processes, which involve the modification on the hybridization of a previously functionalized carbonyl compound. Using this straightforward synthetic strategy, a wide range of valuable chiral building blocks such as α-amino acids, α-amino alcohols, epoxides, 1,2-diols, α-sulfenylated, α-selenenylated and α-halogenated carbonyl derivatives can be obtained by this simple and advantageous methodology.

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“…The key step of the synthesis was the aziridination of , -unsaturated aldehyde 51 organocatalyzed by chiral diphenylprolinol triethylsilyl ether 52 in the presence of three equivalents of a base, such as NaOAc, allowing the key intermediate aziridine 53 to be obtained in 94% yield and 97% ee (Scheme 23) [37]. The latter was subsequently converted into the desired (R)-sumanirole.…”

Section: Organocatalyzed Nitrene Transfer To Alkenesmentioning

confidence: 99%

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Dalpozzo¹,

Lattanzi

Pellissier

2017

COC

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This review updates recent applications of asymmetric aziridination, azirination, thiirination, epoxidation, and cyclopropanation in the total synthesis of biologically active compounds, including natural products, using chiral substrates or chiral catalysts, covering the literature since 2000. The interest towards these synthetic methodologies of chiral three-membered rings has increased in the last decade, dictated either by the biological activities that display many naturally occurring products bearing a three-membered unit or by the ring strain of three-membered rings making them useful precursors of many more complex interesting molecules. Classic as well as modern protocols in asymmetric aziridinations, azirinations, epoxidations, thiirinations, and cyclopropanations have been widely applied as key steps of a number of syntheses of important products. Although the use of chiral substrates and auxiliaries is still highly employed particularly in asymmetric aziridination and cyclopropanation, the development of enantioselective catalytic methodologies has witnessed exponential growth during the last decade. The present review is subdivided into three parts, dealing successively with the use of chiral nitrogen-containing three-membered rings, chiral epoxides and thiiranes, and chiral cyclopropanes in total synthesis.

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Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

Cited by 73 publications

References 39 publications

Organocatalytic Asymmetric Aza‐Michael Additions

Organocatalytic Asymmetric Aza‐Michael Additions

Recent Advances on the Organocatalyzed Enantioselective α-heterofunctionalization of Carbonyl Compounds

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

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Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

Cited by 73 publications

References 39 publications

Organocatalytic Asymmetric Aza‐Michael Additions

Organocatalytic Asymmetric Aza‐Michael Additions

Recent Advances on the Organocatalyzed Enantioselective &#945;-heterofunctionalization of Carbonyl Compounds

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

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Product

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Recent Advances on the Organocatalyzed Enantioselective α-heterofunctionalization of Carbonyl Compounds