Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*,3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy)buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction
Date issued
2010
In
J. Chem. Crystallogr.
Vol
1
No
40
From page
10
To page
14
Subjects
Chiral induction (Felkin-Anh stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) Ethers Role: PEP (Physical engineering or chemical process) RCT (Reactant) PROC (Process) RACT (Reactant or reagent) (enol silyl stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) Dimers Role: FMU (Formation unclassified) PEP (Physical engineering or chemical process) PRP (Properties) FORM (Formation nonpreparative) PROC (Process) (hydrogen-bonded stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) Aldol addition (stereoselective stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) Chemical chains Crystal structure Hydrogen bond Molecular structure Mukaiyama aldol reaction Stereochemistry Supramolecular structure Transition state structure (stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) Hydrogen bond (weak stereoselectivity dichotomy of Mukaiyama reaction and crystallog. of rac-(2R* 3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate and rac-(2R* 3R*)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate) rac ethylchlorohydroxyphenylbuthanethioate ethylphenyltosyloxybuthanethioate dichotomy stereoselectivity Mukaiyama crossed aldol crystallog
Abstract
The compds., rac-(2R*,3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate (I) and rac-(2R*,3R*)-S-ethyl-3-hydroxy-2-phenylbuthanethioate (II), were prepd. by the Mukaiyama crossed aldol reaction between the silyl enol ether of S-Et 2-phenylethanethioate and simple aldehydes, like 2-chloroacetaldehyde (for I) and acetaldehyde (for II). The stereoselectivity of the Mukaiyama aldol reaction has switched from a syn selective process for the reaction using 2-chloroacetaldehyde to an anti selective process for the reaction with acetaldehyde. [on SciFinder(R)]
Publication type
journal article