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Facile and efficient enantioselective Strecker reaction of ketimines by chiral sodium phosphate.
Chemistry. 2009 Jun 08; 15(24):6008-14.C

Abstract

A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol % BNPNa (BNP = 1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol % para-tert-butyl-ortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee = enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from beta-acetonaphthone, alpha-indanone, and alpha-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthyl-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shen K
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Liu X
No affiliation info available
Cai Y
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

CatalysisCyanidesIminesMetals, AlkaliMolecular StructureNaphthalenesNitrilesOrganophosphatesPhosphatesStereoisomerismTrimethylsilyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

19418513

Citation

Shen, Ke, et al. "Facile and Efficient Enantioselective Strecker Reaction of Ketimines By Chiral Sodium Phosphate." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 24, 2009, pp. 6008-14.
Shen K, Liu X, Cai Y, et al. Facile and efficient enantioselective Strecker reaction of ketimines by chiral sodium phosphate. Chemistry. 2009;15(24):6008-14.
Shen, K., Liu, X., Cai, Y., Lin, L., & Feng, X. (2009). Facile and efficient enantioselective Strecker reaction of ketimines by chiral sodium phosphate. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(24), 6008-14. https://doi.org/10.1002/chem.200900210
Shen K, et al. Facile and Efficient Enantioselective Strecker Reaction of Ketimines By Chiral Sodium Phosphate. Chemistry. 2009 Jun 8;15(24):6008-14. PubMed PMID: 19418513.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Facile and efficient enantioselective Strecker reaction of ketimines by chiral sodium phosphate. AU - Shen,Ke, AU - Liu,Xiaohua, AU - Cai,Yunfei, AU - Lin,Lili, AU - Feng,Xiaoming, PY - 2009/5/7/entrez PY - 2009/5/7/pubmed PY - 2009/8/19/medline SP - 6008 EP - 14 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 24 N2 - A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol % BNPNa (BNP = 1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol % para-tert-butyl-ortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee = enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from beta-acetonaphthone, alpha-indanone, and alpha-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthyl-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19418513/Facile_and_efficient_enantioselective_Strecker_reaction_of_ketimines_by_chiral_sodium_phosphate_ L2 - https://doi.org/10.1002/chem.200900210 DB - PRIME DP - Unbound Medicine ER -