Thiol and Disulfide Derivatives of Ephedra Alkaloids 2: A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde

Kevin Fitzpatrick; Ron Hulst; Richard M. Kellogg

doi:10.1016/0957-4166(95)00237-J

Thiol and Disulfide Derivatives of Ephedra Alkaloids 2: A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde

Kevin Fitzpatrick, Ron Hulst, Richard M. Kellogg

Stratingh Institute for Chemistry

Research output: Contribution to journal › Comment/Letter to the editor › Academic › peer-review

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Abstract

Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a high degree of aggregation of the zinc thiolates. The behaviour of the thiol derivatives deviates sharply from that of the oxygen analogue, N-methyl ephedrine.

Original language	English
Pages (from-to)	1861-1864
Number of pages	4
Journal	Tetrahedron-Asymmetry
Volume	6
Issue number	8
DOIs	https://doi.org/10.1016/0957-4166(95)00237-J
Publication status	Published - Aug-1995

Keywords

ENANTIOSELECTIVE ADDITION
ASYMMETRIC-SYNTHESIS
DIALKYLZINCS
ALDEHYDES
ALCOHOLS

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title = "Thiol and Disulfide Derivatives of Ephedra Alkaloids 2: A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde",

abstract = "Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a high degree of aggregation of the zinc thiolates. The behaviour of the thiol derivatives deviates sharply from that of the oxygen analogue, N-methyl ephedrine.",

keywords = "ENANTIOSELECTIVE ADDITION, ASYMMETRIC-SYNTHESIS, DIALKYLZINCS, ALDEHYDES, ALCOHOLS",

author = "Kevin Fitzpatrick and Ron Hulst and Kellogg, {Richard M.}",

note = "Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute",

year = "1995",

month = aug,

doi = "10.1016/0957-4166(95)00237-J",

language = "English",

volume = "6",

pages = "1861--1864",

journal = "Tetrahedron-Asymmetry",

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TY - JOUR

T1 - Thiol and Disulfide Derivatives of Ephedra Alkaloids 2

T2 - A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde

AU - Fitzpatrick, Kevin

AU - Hulst, Ron

AU - Kellogg, Richard M.

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 1995/8

Y1 - 1995/8

N2 - Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a high degree of aggregation of the zinc thiolates. The behaviour of the thiol derivatives deviates sharply from that of the oxygen analogue, N-methyl ephedrine.

AB - Thiol and disulfide derivatives of ephedrine have been shown previously to catalyse in high enantiomeric excess (ee) the reaction of diethyl zinc with benzaldehyde. We find that this reaction involves non-linear correlations between the ee of product and catalyst. Osmotic measurements indicate a high degree of aggregation of the zinc thiolates. The behaviour of the thiol derivatives deviates sharply from that of the oxygen analogue, N-methyl ephedrine.

KW - ENANTIOSELECTIVE ADDITION

KW - ASYMMETRIC-SYNTHESIS

KW - DIALKYLZINCS

KW - ALDEHYDES

KW - ALCOHOLS

U2 - 10.1016/0957-4166(95)00237-J

DO - 10.1016/0957-4166(95)00237-J

M3 - Comment/Letter to the editor

SN - 0957-4166

VL - 6

SP - 1861

EP - 1864

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 8

ER -

Thiol and Disulfide Derivatives of Ephedra Alkaloids 2: A Mechanistic Study of Their Effect on the Addition of Diethyl Zinc to Benzaldehyde

Abstract

Keywords

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