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Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols
Li, CT (Li, Chun-Tian); Liu, H (Liu, Hui); Xu, YJ (Xu, Yan-Jun); Lu, CD (Lu, Chong-Dao)
2017
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume82Issue:20Pages:11253-11261
Abstract

Diastereoselective aldol reaction of N-tert-butanesulfinyl imidates under typical hard enolization conditions is reported. Potassium bis(trimethylsilyl)amide (KHMDS) effectively promotes the aldol reaction of alpha-aryl- and alpha-alkyl-substituted imidates, providing anti-aldol adducts in high yields with good to excellent diastereoselectivities. In the case of alpha-aryl imidates, high conversion depends on adding trimethylsilyl chloride (TMSCI) to the reaction,, Mixture. In the presence of a suitable Lewis acid, cyclohexanone is a good electrophile in the aldol reaction of imidates.

DOI10.1021/acs.joc.7b01982
Indexed BySCI
WOS IDWOS:000413710100052
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Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5030
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD (Lu, Chong-Dao)
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
Li, CT ,Liu, H ,Xu, YJ ,et al. Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols[J]. JOURNAL OF ORGANIC CHEMISTRY,2017,82(20):11253-11261.
APA Li, CT ,Liu, H ,Xu, YJ ,&Lu, CD .(2017).Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols.JOURNAL OF ORGANIC CHEMISTRY,82(20),11253-11261.
MLA Li, CT ,et al."Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols".JOURNAL OF ORGANIC CHEMISTRY 82.20(2017):11253-11261.
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