A Synthetic Route to Sodium α-Aminoalkanesulfinates and Their Application in the Generation of α-Aminoalkyl Radicals for Radical Addition Reactions

Sakamoto, Ryu; Yoshii, Tomomi; Takada, Hiroyuki; Maruoka, Keiji

doi:10.1021/acs.orglett.8b00621

Cited by 15 publications

(8 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[361] Analogously, aminoalkyl-substituted sulfinate derivatives 78 were obtained by lithiation of carbamates 79, followed by reaction with DABSO (Scheme 43B). [384] The method worked only partially for the higher homologues of 79: the corresponding sulfinates were generated in situ and used in the next step.…”

Section: Synthesis Of Sulfinatesmentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

View full text Add to dashboard Cite

Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into the target molecules. The last decade witnessed an emergence of many novel (or well-overlooked old) chemotypes for drug discovery, which is related to adapting new synthetic methodologies, designing new sp 3 -enriched bioisosteres, paying attention to previously underrated (or even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey of selected chemotypes that emerged recently in medicinal chemistry is provided, with a focus on the synthesis of the corresponding building blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non-classical sp 3 -enriched benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well as gemdifluorinated cycloalkanes (as an example of emerging fluorinated motifs) are discussed.

show abstract

Section: Synthesis Of Sulfinatesmentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

View full text Add to dashboard Cite

show abstract

“…Synthesis of phenanthridines 98 through the radical addition/Cyclization was reported by Keiji Maruoka and coworkers in 2018. [63] In this reports they disclosed a synthetic route to sodium alpha-amino-alkane sulfinates 97 and their application in the generation of alpha-amino alkyl radicals for radical addition reaction (Scheme 44). The radical addition/ cyclization to 2-isocyanobiphenyls 1 with sodium alpha-aminoalkane sulfinates 97 afforded the corresponding phenanthridine-6-ylmethanamines 98, which acts as fundamental frag- ments for luminescent probes.…”

Section: Synthesis Of Phenanthridine Derivatives Via Radical Isonitri...mentioning

confidence: 99%

Recent Advancements in Synthesis of Phenanthridines via 2‐Isocyanobiphenyls

Dey,

Kumar,

Chatterjee

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

Phenanthridines are a privileged heterocyclic compound that exists in many natural products and has been known to exhibit a variety of pharmacological properties. In the last few decades, an incredible development has taken place to synthesise this scaffold. In this regard, 2‐isocyanobiphenyl has become one of the most exploited substrates that allow the direct formation of phenanthridine derivatives under various novel and conventional methods. The present review provides an overview of synthetic approaches for the preparation of phenanthridine and their derivatives form 2‐isocyanobiphenyl.

show abstract

“…Simultaneously, Maruoka and co-workers 41 described a new two-step protocol for preparing sodium α-aminoalkane-sulfinate salts, as shown in Scheme 11 . Various N -Boc-protected dialkylamines were treated with sec -BuLi to generate an α-lithiated alkyl-amine that was successfully trapped with DABSO, aqueous workup with sodium carbonate to provide sodium α-aminoalkanesulfinates in variable yields.…”

Section: Synthesis Of Sodium Sulfinatesmentioning

confidence: 99%