PREPARATION OF<i>TRANS</i>-1,2-DIAMINOCYCLOHEXANE DERIVATIVES BY LITHIUM PERCHLORATE CATALYZED RING OPENING OF AZIRIDINES

Parrodi, Cecilia Anaya de; Vázquez, Verónica Patricia Rodríguez; Quintero, Leticia; Juaristi, Eusebio

doi:10.1081/scc-100106039

Cited by 17 publications

(3 citation statements)

References 17 publications

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“…Amino alcohol 5e was formed as a 1:1 diastereomeric mixture, and optimization attempts with perchloric acid failed. Also, LiClO 4 was ineffective for this transformation . Turning to Lewis acids, InCl 3 at pH 4 gave a 2:1 mixture of 6e and 5e , i.e., the unwanted diastereomer was the major compound.…”

Section: Resultsmentioning

confidence: 99%

A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

Olofsson

Somfai

2002

J. Org. Chem.

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Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

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Section: Resultsmentioning

confidence: 99%

A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

Olofsson

Somfai

2002

J. Org. Chem.

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“…All other chemicals were purchased from Aldrich or Strem and used with no further purification unless otherwise noted. The syntheses and spectral data for compounds 1 , 4 , 6d , 6e , cis- and trans - 9a , 9b , and 12 have been reported previously. ,,− Appropriate precautions were taken because 2-methylaziridine, according to Aldrich, is highly toxic and a cancer suspect agent.…”

Section: Methodsmentioning

confidence: 99%

Iron Carbonyl Promoted Conversion of an Aziridine and an Amine Oxide to a 1,2-Diamine

Hancock

Pinhas

2002

Organometallics

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The conversion of an aziridine to a 1,2-diamine using an iron carbonyl complex and an amine oxide is studied. We have found that when the aziridine is substituted by only alkyl groups, it is the less substituted carbon−nitrogen bond that is broken, whereas, when the aziridine is substituted by a phenyl group at either the nitrogen or the carbon, it is the more substituted carbon−nitrogen bond that is broken. With a 2,3-disubstituted aziridine, the reaction proceeds with net retention of stereochemistry. Because the nitrogen in the amine oxide is trisubstituted and the same nitrogen in the product is disubstituted, various amine oxides have been tried to determine the preference for which group will be removed. We have shown that the intermediate iron complex will react with an iminium salt to give the exact same product as is obtained from the corresponding amine oxide.

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“…As expected, the ring opening of the aziridine ring was stereoselective, leading to diamines trans-106-110, with no evidence for the formation of the cis products (Scheme 24). 47 Using the protocol already described, we also reported the synthesis of other cyclic 1,2-diamines derived from cyclopentene oxide, 1,4-cyclohexadiene monoxide, and (S)-1phenylethylamine, affording 1,2-cyclic diamines 111-114 (Scheme 25). 48 A similar methodology was reported almost simultaneously by Periasamy et al, 49 who prepared amino alcohols 115 by refluxing cyclohexene oxide with secondary amines such as pyrrolidine, piperidine and dimethylamine.…”

Section: Synthesis Of Enantiopure Cyclic 12-diaminesmentioning

confidence: 99%

Chiral 1,2-Amino Alcohols and 1,2-Diamines Derived from Cyclohexene Oxide: Recent Applications in Asymmetric Synthesis

Parrodi¹,

Juaristi²

2006

Synlett

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This Account describes convenient procedures for the preparation of several enantiopure b-amino alcohols and b-diamines, which have proved to be efficient ligands in relevant stereoselective reactions such as alkylation of enolates and hydrogenation of carbonyl compounds. Furthermore, the title compounds are useful precursors of various chiral oxazolidinones, oxazinones, phosphonamides, etc., which allow the enantioselective formation of a wide variety of chiral derivatives, including alcohols, aldol condensation products, aminophosphonic acids, sulfoxides, and others, as well as the development of derivatizing reagents for the determination of enantiomeric purity in chiral alcohols and chiral amines.

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PREPARATION OFTRANS-1,2-DIAMINOCYCLOHEXANE DERIVATIVES BY LITHIUM PERCHLORATE CATALYZED RING OPENING OF AZIRIDINES

Cited by 17 publications

References 17 publications

A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

Iron Carbonyl Promoted Conversion of an Aziridine and an Amine Oxide to a 1,2-Diamine

Chiral 1,2-Amino Alcohols and 1,2-Diamines Derived from Cyclohexene Oxide: Recent Applications in Asymmetric Synthesis

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