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Diastereoselective synthesis of 2-methoxyimidoyl-oxiranes via dimethyl phosphite-mediated coupling of alpha-keto N-sulfinyl imidates with aldehydes
Huang, W (Huang, Wei); Liu, H (Liu, Hui); Lu, CD (Lu, Chong-Dao); Xu, YJ (Xu, Yan-Jun); Lu, CD
2016
Source PublicationCHEMICAL COMMUNICATIONS
ISSN1359-7345
Volume52Issue:93Pages:13592-13595
Abstract

Dimethyl phosphite-initiated coupling of alpha-keto N-tert-butylsulfinyl imidates with aldehydes is reported. The epoxide formation involves a cascade transformation initiated by base-promoted addition of phosphite to a-ketoimidates, followed by [1,2]-phospha-Brook rearrangement. This generates a-phosphonyloxy enolates that are subsequently intercepted by aldehydes, leading to [1,4] O-O dialkoxyphosphinyl migration and finally to intramolecular ring closure. This protocol was used to synthesize a range of enantioenriched trans-alpha, beta-epoxy imidates in moderate to high yields with excellent diastereoselectivities.

DOI10.1039/C6CC07723D
Indexed BySCI
WOS IDWOS:000388613600012
Citation statistics
Cited Times:9[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4690
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD
Affiliation1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Huang, W ,Liu, H ,Lu, CD ,et al. Diastereoselective synthesis of 2-methoxyimidoyl-oxiranes via dimethyl phosphite-mediated coupling of alpha-keto N-sulfinyl imidates with aldehydes[J]. CHEMICAL COMMUNICATIONS,2016,52(93):13592-13595.
APA Huang, W ,Liu, H ,Lu, CD ,Xu, YJ ,&Lu, CD.(2016).Diastereoselective synthesis of 2-methoxyimidoyl-oxiranes via dimethyl phosphite-mediated coupling of alpha-keto N-sulfinyl imidates with aldehydes.CHEMICAL COMMUNICATIONS,52(93),13592-13595.
MLA Huang, W ,et al."Diastereoselective synthesis of 2-methoxyimidoyl-oxiranes via dimethyl phosphite-mediated coupling of alpha-keto N-sulfinyl imidates with aldehydes".CHEMICAL COMMUNICATIONS 52.93(2016):13592-13595.
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