NDLI: 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

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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

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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

Content Provider	Springer Nature Link
Author	Vallat, Oliver Buciumas, Ana Maria Neier, Reinhard Stoeckli Evans, Helen
Copyright Year	2009
Abstract	The title compounds, rac-(2R,3R)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate (I) and rac-(2R,3R)-S-ethyl-2-phenyl-3-(tosyloxy)buthanethioate (III), are both composed of a S-ethyl 2-phenylbutanethioate moiety but have different geometries. Compound I is substituted in the 3 and 4 positions by a hydroxyl group and a chlorine atom, respectively. In compound III the hydroxyl group in the 3 position of rac-(2R,3R)-S-ethyl-3-hydroxy-2-phenylbuthanethioate (II), has been tosylated in order to obtain suitable crystals for X-ray analysis. In compound I the phenyl substituent and the hydroxyl group have a syn arrangement, whereas in the tosylate derivative of II, i.e., compound III, they have an anti arrangement. In the crystal structure of I centrosymmetric hydrogen bonded dimers are formed via O–H···O hydrogen bonds, involving the hydroxyl group and the carbonyl O-atom. In the crystal structure of III symmetry related molecules are connect via a weak C–H···O intermolecular interaction, involving a tosylate O-atom and a phenyl H-atom, so forming zigzag chains propagating in the c direction. The compounds were prepared by the Mukaiyama crossed aldol reaction between the silyl enol ether of S-ethyl 2-phenylethanethioate and simple aldehydes, like 2-chloroacetaldehyde (for I) and acetaldehyde (for II). The syn/anti stereo descriptors clearly indicate that 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. In both compounds the relative stereochemistry at the newly created chiral centers, positions 2 and 3, is R/R.The compounds, rac-(2R,3R)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate (I) and rac-(2R,3R)-S-ethyl-3-hydroxy-2-phenylbuthanethioate (II), were prepared by the Mukaiyama crossed aldol reaction between the silyl enol ether of S-ethyl 2-phenylethanethioate and simple aldehydes, like 2-chloroacetaldehyde (for I) and acetaldehyde (for II). The stereoselectivity of the Mukaiyama aldol reaction was shown to have switched from a syn selective process for the reaction using 2-chloroacetaldehyde to an anti selective process for the reaction with acetaldehyde.
Starting Page	10
Ending Page	14
Page Count	5
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	40
Issue Number	1
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2009-08-18
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Mukaiyama aldol reaction Stereoselectivity X-ray analysis Hydrogen bonding Inorganic Chemistry Physical Chemistry Crystallography Organometallic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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