132587-07-6Relevant articles and documents
Synthesis of highly functionalized δ-lactone-fused cyclopentanoids
Khan, Faiz Ahmed,Krishnakumar,Sudheer
, p. 1054 - 1060 (2007)
A short and efficient route to δ-lactone-fused cyclopentanoids starting from the easily accessible Diels-Alder adducts between homoallylic alcohol acetates and 1,2,3,4-tetrachloro-5,5-dimethoxycyclopenta-1,3-diene is reported. Since homoallyl alcohols wer
LiBF4-Catalyzed three-component coupling of an aldehyde, acetic anhydride and allyltrimethylsilane/TMSCN
Yadav,Reddy, B.V. Subba,Vishnumurthy,Chary, Ch. Janardhana
, p. 5915 - 5918 (2007)
Lithium tetrafluoroborate is found to be an efficient catalyst for allylation and cyanation of aldehydes with allyltrimethylsilane and trimethylsilyl cyanide in the presence of acetic anhydride at room temperature to produce homoallylic acetates and α-cya
A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
Kanojia, Seema V.,Chatterjee, Sucheta,Chattopadhyay, Subrata,Goswami, Dibakar
, p. 490 - 496 (2019)
A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF6], followed by a diastereoselective asymmetric dihydroxylatio
Highly Focused Library-Based Engineering of Candida antarctica Lipase B with (S)-Selectivity Towards sec-Alcohols
Cen, Yixin,Li, Danyang,Xu, Jian,Wu, Qiongsi,Wu, Qi,Lin, Xianfu
supporting information, p. 126 - 134 (2018/12/05)
Candida antarctica lipase B (CALB) is one of the most extensively used biocatalysts in both academia and industry and exhibits remarkable (R)-enantioselectivity for various chiral sec-alcohols. Considering the significance of tailor-made stereoselectivity in organic synthesis, a discovery of enantiocomplementary lipase mutants with high (R)- and (S)-selectivity is valuable and highly desired. Herein, we report a highly efficient directed evolution strategy, using only 4 representative amino acids, namely, alanine (A), leucine (L), lysine (K), tryptophan (W) at each mutated site to create an extremely small library of CALB variants requiring notably less screening. The obtained best mutant with three mutations W104V/A281L/A282K displayed highly reversed (S)-selectivity towards a series of sec-alcohol with E values up to 115 (conv. 50%, ee 94%). Compared with the previously reported (S)-selective CALB variant, W104A, a single mutation provided less selectivity, while the synergistic effects of three mutations in the best variant endow better (S)-selectivity and a broader substrate scope than the W104A variant. Structural analysis and molecular dynamics simulation unveiled the source of reversed enantioselectivity. (Figure presented.).
Dynamic kinetic resolution of homoallylic alcohols: Application to the synthesis of enantiomerically pure 5,6-dihydropyran-2-ones and δ-lactones
Warner, Madeleine C.,Shevchenko, Grigory A.,Jouda, Suzan,Bogar, Krisztian,Baeckvall, Jan-E.
, p. 13859 - 13864 (2013/10/22)
Dynamic kinetic resolution of various homoallylic alcohols with the use of Candida antarctica lipase B and ruthenium catalyst 2 afforded homoallylic acetates in high yields and with high enantioselectivity. These enantiopure acetates were further transfor
