α-Haloketones,α-Haloaldehydes andα-Haloimines (1988)

Kimpe, Norbert De; Verh, Roland

doi:10.1002/9780470772157

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Cited by 134 publications

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The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

Ding

Huang

1999

Heteroatom Chem.

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A new pathway for the reaction involving an α‐haloketone and a dialkyl phosphite has been suggested, It offers a highly stereoselective synthetic procedure leading to β‐haloenol phosphates in one‐pot reactions that take place in good yields. However, normal Pudovik reaction products were formed when the reaction was carried out using a relatively small amount of base. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 55–59, 1999

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The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

Ding

Huang

1999

Heteroatom Chem.

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Consequences of the Preeminent Reactivity of 2-OH in Sucrose: Cyclic Acetalation at 2-OH and 3-OH under Basic Conditions

Giry-Panaud¹,

Descotes²,

Bouchu³

et al. 1999

Eur. J. Org. Chem.

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The reaction of unprotected sucrose with tert‐butyl chloromethyl ketone in dimethylformamide was investigated as a model for the study of the relative reactivity of the various hydroxy groups of sucrose. Besides the monoethers arising from the substitution of the chlorine atom by 2‐OH and 1′‐OH of sucrose, the major product is a tert‐butyl hydroxymethyl 5‐membered ring acetal involving 2‐OH and 3‐OH. The formation of this product illustrates the preeminent reactivity of 2‐OH towards the carbonyl group of the α‐chloromethyl ketone, leading to an intermediate hemiacetalic anion, which can enter by intramolecular acetal formation through an intermediate epoxide.

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Bromoacetone

Kimpe

2001

Encyclopedia of Reagents for Organic Synthesis

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α-Haloketones,α-Haloaldehydes andα-Haloimines (1988)

Cited by 134 publications

References 0 publications

The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

The stereoselective synthesis of ?-haloenol phosphates?A reinvestigation of the reaction of ?-haloketones with diethyl phosphite

Consequences of the Preeminent Reactivity of 2-OH in Sucrose: Cyclic Acetalation at 2-OH and 3-OH under Basic Conditions

Bromoacetone

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