A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde.Chem Asian J. 2015 Dec; 10(12):2701-7.CA
Abstract
A direct, concise, and enantioselective synthesis of 2-substituted 4,4,4-trifluorobutane-1,3-diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol %) of commercially available and inexpensive l-prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0 °C, followed by reduction with sodium borohydride, gives 2-substituted 4,4,4-trifluorobutane-1,3-diols in moderate to good yields (31-84%) with low diastereoselectivities and good to excellent enantioselectivities (64-97% ee).
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MeSH
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
26206587
Citation
Funabiki, Kazumasa, et al. "A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based On the Organocatalytic in Situ Generation of Unstable Trifluoroacetaldehyde." Chemistry, an Asian Journal, vol. 10, no. 12, 2015, pp. 2701-7.
Funabiki K, Furuno Y, Yano Y, et al. A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde. Chem Asian J. 2015;10(12):2701-7.
Funabiki, K., Furuno, Y., Yano, Y., Sakaida, Y., Kubota, Y., & Matsui, M. (2015). A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde. Chemistry, an Asian Journal, 10(12), 2701-7. https://doi.org/10.1002/asia.201500607
Funabiki K, et al. A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based On the Organocatalytic in Situ Generation of Unstable Trifluoroacetaldehyde. Chem Asian J. 2015;10(12):2701-7. PubMed PMID: 26206587.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - A Direct, Concise, and Enantioselective Synthesis of 2-Substituted 4,4,4-Trifluorobutane-1,3-diols Based on the Organocatalytic In Situ Generation of Unstable Trifluoroacetaldehyde.
AU - Funabiki,Kazumasa,
AU - Furuno,Yudai,
AU - Yano,Yosuke,
AU - Sakaida,Yuta,
AU - Kubota,Yasuhiro,
AU - Matsui,Masaki,
Y1 - 2015/08/17/
PY - 2015/06/11/received
PY - 2015/7/25/entrez
PY - 2015/7/25/pubmed
PY - 2016/10/8/medline
KW - aldol reaction
KW - asymmetric synthesis
KW - fluorine
KW - organocatalysis
KW - synthesis design
SP - 2701
EP - 7
JF - Chemistry, an Asian journal
JO - Chem Asian J
VL - 10
IS - 12
N2 - A direct, concise, and enantioselective synthesis of 2-substituted 4,4,4-trifluorobutane-1,3-diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol %) of commercially available and inexpensive l-prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0 °C, followed by reduction with sodium borohydride, gives 2-substituted 4,4,4-trifluorobutane-1,3-diols in moderate to good yields (31-84%) with low diastereoselectivities and good to excellent enantioselectivities (64-97% ee).
SN - 1861-471X
UR - https://www.unboundmedicine.com/medline/citation/26206587/A_Direct_Concise_and_Enantioselective_Synthesis_of_2_Substituted_444_Trifluorobutane_13_diols_Based_on_the_Organocatalytic_In_Situ_Generation_of_Unstable_Trifluoroacetaldehyde_
DB - PRIME
DP - Unbound Medicine
ER -
