72959-50-3Relevant articles and documents
Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters
Sun, Jun,Yoshiiwa, Toshiya,Iwata, Takayuki,Shindo, Mitsuru
supporting information, p. 6585 - 6588 (2019/09/30)
Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.
Scandium Trifluoromethanesulfonate as an Extremely Active Acylation Catalyst
Ishihara, Kazuaki,Kubota, Manabu,Kurihara, Hideki,Yamamoto, Hisashi
, p. 4413 - 4414 (2007/10/02)
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ACYCLIC STEREOSELECTION-13; ARYL ESTERS: REAGENTS FOR THREO-ALDOLIZATION
Heathcock, Clayton H.,Pirrung, Michael C.,Montgomery, Stephen H.,Lampe, John
, p. 4087 - 4095 (2007/10/02)
Preformed Li enolates of hindered aryl esters condense with aldehydes to give predominantly threo aldols.The method has been explored with esters 3 (DMP propionate), 4 (BHT propionate), 5 (DBHA propionate).DMP propionate reacts with benzaldehyde and α-unbranched aliphatic aldehydes to give threo:erythro ratios of about 6.5:1.However, with α-branched aliphatic aldehydes, ester 3 gives only threo-aldols.BHT propionate and DBHA propionate give only threo-aldols with all aldehydes studied.The DMP aldols may be converted into β-hydroxy acids by simple hydrolysis with KOH in aqueous methanol.BHT aldols cannot be hydrolyzed without retroaldolization.However, these aldols can be reduced to diastereomerically pure 1,3-diols.The DBHA aldols can converted into β-hydroxy acids by a method involving oxidation with ceric ammonium nitrate (CAN) in aqueous acetonitrile.Threo-selectivity is also seen in the condensations of DMP butyrate (15), DBHA butyrate (16), DMP pentenoate (17), and BHT pentenoate (18).The approach has been utilized in a stereoselective synthesis of racemic methyl corynomycolate.