Garcia Ruano, Jose L. published the artcileHighly Stereoselective Aldol Reactions of Lithium Ester Enolates with (RS)-2-(p-Tolylsulfinyl)cyclohexanones, Application In Synthesis of 5340-78-3, the publication is Journal of Organic Chemistry (1996), 61(26), 9462-9470, database is CAplus.
Aldol reactions of lithium alkyl acetates (LiCRR”CO2R’) with (RS)-2-(p-tolylsulfinyl)cyclohexanone (1) (as an epimeric mixture at C-2) take place with very efficient control of the configuration at the tertiary hydroxylic carbon (C-1). Stereoselectivity becomes complete if R and/or R” are not hydrogen. Only carbinols derived from the (S2,RS)-1 epimer were obtained, the major ones being those exhibiting the S configuration (opposite to that of the sulfur) at the hydroxylic carbon. When LiCHRCO2R’ is used, mixtures of the two epimers at the new stereogenic center C-1′ are obtained (∼10-82% de), their proportion being dependent on the size of R. The use of lactone enolates avoids the formation of epimeric mixtures, affording only one diastereoisomer with an (R3′,S1,S2,RS) configuration at the four adjacent chiral centers. Tricoordinated lithium species, which involve the enolate and the sulfinyl and carbonyl oxygens of the substrates, are invoked to explain the stereoselectivity observed in these aldol reactions with sulfinyl ketones as electrophiles.
Journal of Organic Chemistry published new progress about 5340-78-3. 5340-78-3 belongs to esters-buliding-blocks, auxiliary class Aliphatic Chain, name is Ethyltert-butylacetate, and the molecular formula is C8H16O2, Application In Synthesis of 5340-78-3.
Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics