ICCAS OpenIR
Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes
Li, Jiuyuan; Fu, Niankai; Li, Xin; Luo, Sanzhong; Cheng, Jin-Pei
2010-07-02
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume75Issue:13Pages:4501-4507
AbstractHighly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary-tertiary diamine-Bronsted acid salts are found to promote the cross-aldol reactions of aldehydes with high activity and syn selectivity. Among various vicinal diamines screened, L-phenylalanine derived 2a/TfOH conjugate is identified as the optimal catalyst, showing good catalytic activity (up to 97% yield) and high syn selectivities (syn/anti up to 24: I, 87% cc). The current catalysis works selectively with small aliphatic aldehydes donors such as propionaldehyde and isobutyraldehyde, but not with aliphatic aldehydes bearing larger beta-substitute (> Me). In addition, the use of 2a/TfOH conjugate has also enabled the first syn-selective cross-aldol reactions of glycoaldehyde donors.
DOI10.1021/jo100976e
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000279030900018
PublisherAMER CHEMICAL SOC
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/69994
Collection中国科学院化学研究所
Corresponding AuthorLuo, Sanzhong
AffiliationChinese Acad Sci, BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Li, Jiuyuan,Fu, Niankai,Li, Xin,et al. Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes[J]. JOURNAL OF ORGANIC CHEMISTRY,2010,75(13):4501-4507.
APA Li, Jiuyuan,Fu, Niankai,Li, Xin,Luo, Sanzhong,&Cheng, Jin-Pei.(2010).Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes.JOURNAL OF ORGANIC CHEMISTRY,75(13),4501-4507.
MLA Li, Jiuyuan,et al."Chiral Primary-Tertiary-Diamine-Bronsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes".JOURNAL OF ORGANIC CHEMISTRY 75.13(2010):4501-4507.
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