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Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes.
Chemistry. 2010 Sep 03; 16(33):10124-9.C

Abstract

An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98 %) with excellent diastereo- (up to >99:1 d.r.) and enantioselectivities (up to >99 % ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol % L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen X
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Zhu Y
No affiliation info available
Qiao Z
No affiliation info available
Xie M
No affiliation info available
Lin L
No affiliation info available
Liu X
No affiliation info available
Feng X
No affiliation info available

MeSH

AldehydesAmino AcidsCatalysisImidesIsothiocyanatesNickelNitrogen OxidesOrganometallic CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20645334

Citation

Chen, Xiaohong, et al. "Efficient Synthesis of Beta-hydroxy-alpha-amino Acid Derivatives Via Direct Catalytic Asymmetric Aldol Reaction of Alpha-isothiocyanato Imide With Aldehydes." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 16, no. 33, 2010, pp. 10124-9.
Chen X, Zhu Y, Qiao Z, et al. Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes. Chemistry. 2010;16(33):10124-9.
Chen, X., Zhu, Y., Qiao, Z., Xie, M., Lin, L., Liu, X., & Feng, X. (2010). Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes. Chemistry (Weinheim an Der Bergstrasse, Germany), 16(33), 10124-9. https://doi.org/10.1002/chem.201000284
Chen X, et al. Efficient Synthesis of Beta-hydroxy-alpha-amino Acid Derivatives Via Direct Catalytic Asymmetric Aldol Reaction of Alpha-isothiocyanato Imide With Aldehydes. Chemistry. 2010 Sep 3;16(33):10124-9. PubMed PMID: 20645334.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient synthesis of beta-hydroxy-alpha-amino acid derivatives via direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes. AU - Chen,Xiaohong, AU - Zhu,Yin, AU - Qiao,Zhen, AU - Xie,Mingsheng, AU - Lin,Lili, AU - Liu,Xiaohua, AU - Feng,Xiaoming, PY - 2010/7/21/entrez PY - 2010/7/21/pubmed PY - 2011/2/12/medline SP - 10124 EP - 9 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 16 IS - 33 N2 - An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98 %) with excellent diastereo- (up to >99:1 d.r.) and enantioselectivities (up to >99 % ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol % L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air-tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/20645334/Efficient_synthesis_of_beta_hydroxy_alpha_amino_acid_derivatives_via_direct_catalytic_asymmetric_aldol_reaction_of_alpha_isothiocyanato_imide_with_aldehydes_ L2 - https://doi.org/10.1002/chem.201000284 DB - PRIME DP - Unbound Medicine ER -