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DOI | 10.1038/s41467-017-02695-7 |
Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst | |
Watile, Rahul A.1; Bunrit, Anon1; Margalef, Jessica1; Akkarasamiyo, Sunisa1; Ayub, Rabia1; Lagerspets, Emi2; Biswas, Srijit3; Repo, Timo2; Samec, Joseph S. M.1 | |
2019-08-23 | |
发表期刊 | NATURE COMMUNICATIONS |
ISSN | 2041-1723 |
出版年 | 2019 |
卷号 | 10 |
文章类型 | Article |
语种 | 英语 |
国家 | Sweden; Finland; India |
英文摘要 | Optically pure alcohols are abundant in nature and attractive as feedstock for organic synthesis but challenging for further transformation using atom efficient and sustainable methodologies, particularly when there is a desire to conserve the chirality. Usually, substitution of the OH group of stereogenic alcohols with conservation of chirality requires derivatization as part of a complex, stoichiometric procedure. We herein demonstrate that a simple, inexpensive, and environmentally benign iron(III) catalyst promotes the direct intramolecular substitution of enantiomerically enriched secondary and tertiary alcohols with O-, N-, and S-centered nucleophiles to generate valuable 5-membered, 6-membered and aryl-fused 6-membered heterocyclic compounds with chirality transfer and water as the only byproduct. The power of the methodology is demonstrated in the total synthesis of (+)-lentiginosine from D-glucose where iron-catalysis is used in a key step. Adoption of this methodology will contribute towards the transition to sustainable and bio-based processes in the pharmaceutical and agrochemical industries. |
领域 | 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000482398900028 |
WOS关键词 | ALLYLIC ALCOHOLS ; NUCLEOPHILIC-SUBSTITUTION ; ALKYLATION ; MECHANISMS ; AMINATION ; SOLVOLYSES ; EFFICIENCY ; AMINES |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
URL | 查看原文 |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/203633 |
专题 | 资源环境科学 |
作者单位 | 1.Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden; 2.Univ Helsinki, Dept Chem, AI Virtasen Aukio 1,POB 55, Helsinki 00014, Finland; 3.Univ Calcutta, Univ Coll Sci, Dept Chem, Kolkata 700009, W Bengal, India |
推荐引用方式 GB/T 7714 | Watile, Rahul A.,Bunrit, Anon,Margalef, Jessica,et al. Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst[J]. NATURE COMMUNICATIONS,2019,10. |
APA | Watile, Rahul A..,Bunrit, Anon.,Margalef, Jessica.,Akkarasamiyo, Sunisa.,Ayub, Rabia.,...&Samec, Joseph S. M..(2019).Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst.NATURE COMMUNICATIONS,10. |
MLA | Watile, Rahul A.,et al."Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron (III) catalyst".NATURE COMMUNICATIONS 10(2019). |
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