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Crystallization-Induced Diastereomer Transformation of α-Bromo α′-Sulfinyl Ketones. Diastereodivergent Synthesis of (+)-α-Conhydrine and (−)-β-Conhydrine

Autor: Erwann Grenet, Pierre-Yves Geant, Xavier J. Salom-Roig

Publikováno v: Organic Letters
Organic Letters, American Chemical Society, 2021, 23 (21), pp.8539-8542. ⟨10.1021/acs.orglett.1c03237⟩

Crystallization-Induced Diastereomer Transformation (CIDT) of α-bromo-α'-(R)-sulfinylketones is reported. This process provides not readily accessible enantiopure stereolabile α-bromoketones, which after diastereoselective carbonyl group reduction

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9618799b79adb7189b6de2f2a6126cd5
https://doi.org/10.1021/acs.orglett.1c03237

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Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine

Autor: Won-Hun Ham, In-Soo Myeong, Jin-Seok Kim, Changyoung Jung, Yong-Taek Lee, Sanghyun Lee

Publikováno v: Tetrahedron. 74:506-511

Stereoselective allylation of N-p-methoxyphenyl (PMP)-substituted α-hydroxy aldimines is described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were employed to mediate the allylation reactions. The addition of the allyl gr

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::e293751385e450cb6b2e5b9aaf9f308b
https://doi.org/10.1016/j.tet.2017.12.024

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Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (−)-swainsonine using an aziridine derived common chiral synthon

Autor: Kailash P. Pawar, Lalit B. Khairnar, Sanket A. Kawale, Prakash N. Chavan, Subhash P. Chavan

Publikováno v: RSC Advances. 5:50580-50590

Concise total syntheses of (R)-pipecolic acid, (R)-ethyl-6-oxopipecolate, (2R,3R)-3-hydroxypipecolic acid and formal syntheses of β-(+)-conhydrine, (−)-lentiginosine, (−)-swainsonine and 1,2-di-epi-swainsonine have been accomplished starting fro

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::f4b70ec474a6e77681569f0fb9b448fd
https://doi.org/10.1039/c5ra06429e

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Stereoselective Synthesis of (+)-α-Conhydrine from R-(+)-Glyceraldehyde

Autor: Nageshwar Rao Penumati, Nagaiah Kommu

Publikováno v: Organic Chemistry International. 2014:1-7

Stereoselective synthesis of (+)-α-Conhydrine was accomplished from protected (R)-(+)-glyceraldehyde, a familiar carbohydrate predecessor. Our synthetic strategy featured the following two key reactions. One is Zn-mediated stereoselective aza-Barbie

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1ce4b3132b3624af3cac5bf51154f809
https://doi.org/10.1155/2014/982716

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Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis

Autor: Sandesh T. Bugde, Chinmay Bhat, Santosh G. Tilve

Publikováno v: Synthesis. 46:2551-2573

Conhydrine is a naturally occurring 2-substituted piperidine alkaloid from the plant Conium maculatum L that exists in four different forms and is known for its high toxicity. This article focuses on the synthesis of conhydrine as its medicinal appli

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::828e82afa447158b2b1615f74ddd2a30
https://doi.org/10.1055/s-0034-1379023

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Formal Synthesis of (+)-α-Conhydrine and Stereoselective Synthesis of Pyrrolidine Analogue via the Diastereoselective Chelation-Controlled Hydride Reduction and Wittig Reaction

Autor: Jong-Cheol Kang, Xiangdan Jin, Won-Hun Ham, Tian Jin, Seok-Hwi Park, Jin-Seok Kim, Yu Mu, Chang-Young Oh

Publikováno v: Synthetic Communications. 44:2401-2408

Asymmetric syntheses of (+)-α-conhydrine and its pyrrolidine analogue were achieved from readily available L-serine. The key step involved highly diastereoselective chelation-controlled hydride reduction of the amino ketone to give the anti-amino al

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::b2a1ddf23627a244424810711f3f58d7
https://doi.org/10.1080/00397911.2014.899605

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Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

Autor: Kavirayani R. Prasad, Vipin Ashok Rangari

Publikováno v: Tetrahedron. 75:130496

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant su

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::46b28f39dd82ce95b31ac5e190dbc469
https://doi.org/10.1016/j.tet.2019.130496

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