Short and simple synthesis of chelating bis-ethers and bis-amines in the bicyclo[3.3.1]nonane series

Chau, Felix; Corey, E. J.

doi:10.1016/j.tetlet.2006.02.038

Cited by 20 publications

(14 citation statements)

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“…We would like to illustrate this very simple idea on the bis-ketal rac-(2,6-diethoxy-1,5-dimethyl-2,6-diphenyl-3,7-dioxa-bicyclo[3.3.1]nonane) 1, which was recently showed by Chau and Corey to form a conglomerate. 7 They separated the crystals by hand and they ''individually subjected (them) to measurement of optical rotation.'' The enantiomers of 1 have not yet been analyzed by HPLC on chiral support.…”

Section: Results and Discussion General Consideration And Warning Formentioning

confidence: 99%

“…7 The crude product was purified by double recrystallization from benzene; colorless crystals (m.p. 2178C) were obtained.…”

Section: Materials and Methods Samplesmentioning

confidence: 99%

“…rac-(2,6-Diethoxy-1,5-dimethyl-2,6-diphenyl-3,7-dioxabicyclo[3.3.1]nonane) 1 was prepared according to the procedure described by Chau and Corey. 7 The crude product was purified by double recrystallization from benzene; colorless crystals (m.p. 2178C) were obtained.…”

Section: Materials and Methods Samplesmentioning

confidence: 99%

“…7 They separated the crystals by hand and they ''individually subjected (them) to measurement of optical rotation.'' The enantiomers of 1 have not yet been analyzed by HPLC on chiral support.…”

Section: Chiral Hplcmentioning

confidence: 99%

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HPLC on chiral support with polarimetric detection: Application to conglomerate discovery

et al. 2007

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In conglomerates, each single crystal contains only one of the two possible enantiomeric forms--either dextrorotatory or levorotatory. The analysis of a single crystal by liquid chromatography on chiral support associated with chiroptical detection is a very efficient tool to reveal the occurrence of a conglomerate. In terms of rapidity and easiness, this method compares favorably with the classical methods used to show this occurrence. Two examples are provided.

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Section: Results and Discussion General Consideration And Warning Formentioning

confidence: 99%

“…7 The crude product was purified by double recrystallization from benzene; colorless crystals (m.p. 2178C) were obtained.…”

Section: Materials and Methods Samplesmentioning

confidence: 99%

Section: Materials and Methods Samplesmentioning

confidence: 99%

Section: Chiral Hplcmentioning

confidence: 99%

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HPLC on chiral support with polarimetric detection: Application to conglomerate discovery

et al. 2007

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“…A conceptually different route to 2,6-diendo-diphenylbispidines of type 93-95 possessing two additional methyl groups at the bridgehead carbons was presented by Corey and Chau (Scheme 16). 68 Successive treatment of propiophenone (88) The two enantiomeric bispidine lactams 101 and ent-101 69 (Schemes 17 and 18) prepared in the Lesma group are of interest as they might provide late-stage precursors for an endo-selective introduction of substituents in a-position to the nitrogen atom; for example, by addition of organometallic reagents after appropriate activation of the amide functionality and subsequent reduction. 70 The synthesis of 101 69 (Scheme 17) started from achiral N-Cbzpiperidine-3,5-dimethanol (meso-96), which was enantio- a n t i a n t i s y n a n t i selectively acetylated using Pseudomonas fluorescens lipase to give the monoalcohol 97 in >98% ee.…”

Section: Chiral Bicyclic Bispidinesmentioning

confidence: 99%

Chiral Bispidines

Breuning¹,

Steiner²

2008

Synthesis

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Chiral bispidines are characterized by a modified 3,7-diazabicyclo[3.3.1]nonane framework. Their structural diversity is broad, reaching from simple bicyclic derivatives with chiral substituents at the nitrogen atoms to sophisticated tetracyclic ones like (-)-sparteine. This review focuses on the stereoselective preparation of chiral bispidines and on their applications in selected asymmetric transformations, thus showing the tremendous progress achieved in both areas over the last 15 years.

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Addition of Organometallic Reagents to Chiral N‐Methoxylactams: Enantioselective Syntheses of Pyrrolidines and Piperidines

Jäkel

Schnitzer

et al. 2013

Chemistry A European J

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Enantioselective iridium-catalyzed allylic substitutions were used to prepare N-allyl hydroxamic acid derivatives that were suitable for ring-closing metathesis, giving N-methoxylactams. Reactions of these derivatives with Grignard or organolithium compounds gave hemiaminals, which could be reduced diastereoselectively via acyliminium intermediates to give cis-piperidines or cis-pyrrolidines with substituents in the 2,6- or 2,5-positions, respectively. In addition, compounds with a quaternary carbon center could be synthesized by corresponding reactions with potassium cyanide/AcOH. The procedures were applied in the syntheses of alkaloids (-)-209D and (+)-prosophylline.

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Short and simple synthesis of chelating bis-ethers and bis-amines in the bicyclo[3.3.1]nonane series

Cited by 20 publications

References 0 publications

HPLC on chiral support with polarimetric detection: Application to conglomerate discovery

HPLC on chiral support with polarimetric detection: Application to conglomerate discovery

Chiral Bispidines

Addition of Organometallic Reagents to Chiral N‐Methoxylactams: Enantioselective Syntheses of Pyrrolidines and Piperidines

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