Category: esters-buliding-blocks. In 2019.0 CHEM SCI published article about HETEROCYCLIC CARBENE BORANES; NMR COUPLING-CONSTANTS; CATALYZED HYDROBORATION; CARBONYL-COMPOUNDS; EFFICIENT; INSERTION; ALKENES; ADDITIONS; ALDEHYDES; ADDUCTS in [Radcliffe, James E.; Fasano, Valerio; Adams, Ralph W.; You, Peiran; Ingleson, Michael J.] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England in 2019.0, Cited 44.0. The Name is Methyl 3-phenyl-2-propenoate. Through research, I have a further understanding and discovery of 103-26-4.
Useful alpha-boryl esters can be synthesized in one step from alpha,beta-unsaturated esters using just a simple to access NHC-BH3 (NHC = N-heterocyclic carbene) and catalytic I-2. The scope of this reductive alpha-borylation methodology is excellent and includes a range of alkyl, aryl substituted and cyclic and acyclic alpha,beta-unsaturated esters. Mechanistic studies involving reductive borylation of a cyclic alpha,beta-unsaturated ester with NHC-BD3/I-2 indicated that concerted hydroboration of the alkene moiety in the alpha,beta-unsaturated ester proceeds instead of a stepwise process involving initial 1,4-hydroboration; this is in contrast to the recently reported reductive alpha-silylation. The BH2(NHC) unit can be transformed into electrophilic BX2(NHC) moieties (X = halide) and the ester moiety can be reduced to the alcohol with the borane unit remaining intact to form b-boryl alcohols. The use of a chiral auxiliary, 8-phenylmenthyl ester, also enables effective stereo-control of the newly formed C-B bond. Combined two step ester reduction/borane oxidation forms diols, including excellent e. e. (97%) for the formation of S-3-phenylpropane-1,2-diol. This work represents a simple transition metal free route to form bench stable alpha-boryl esters from inexpensive starting materials.
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Reference:
Article; Weng, Shiue-Shien; Ke, Chih-Shueh; Chen, Fong-Kuang; Lyu, You-Fu; Lin, Guan-Ying; Tetrahedron; vol. 67; 9; (2011); p. 1640 – 1648;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics