81445-44-5Relevant articles and documents
Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines
Ando, Kaori,Fettinger, James,Gutierrez, David A.,Houk, K. N.,Shaw, Jared T.
supporting information, p. 1164 - 1168 (2022/02/14)
The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.
A Concise Synthesis of the Key Tetrahydrofuran Moieties of Caruifolin A and EBC-342
Fernandes, Rodney A.,Bethi, Venkati
, p. 6922 - 6928 (2020/06/10)
A common strategy for the concise synthesis of the key tetrahydrofuran moieties of caruifolin A and EBC-342 is presented. Asymmetric dihydroxylation and intramolecular SN2-cyclization are key strategic reactions for the synthesis of the furan f
Efficient Stereoselective Synthesis of a Key Chiral Aldehyde Intermediate in the Synthesis of Picolinamide Fungicides
Li, Fangzheng,Good, Steffen,Tulchinsky, Michael L.,Whiteker, Gregory T.
, p. 2253 - 2260 (2019/10/16)
A highly stereoselective and efficient synthesis of (4S,5S,6S)-6-(benzyloxy)-5-phenoxy-4-propoxyheptanal, a key intermediate for syntheses of picolinamide fungicides, is described in this report. The synthesis features a scalable allylpropyl ether preparation, an efficient synthesis of the C1-C3 anti,syn-(S,S,S) stereotriad via a highly diastereoselective allylboration, and Cu-catalyzed phenylation of a sterically hindered secondary alcohol with BiPh3(OAc)2 followed by highly regioselective hydroformylation with the formation of a linear aldehyde. Excellent overall route efficiency was achieved (six steps and 39% yield) starting from readily available and inexpensive (S)-ethyl lactate.
