Enantioselective synthesis of 1-substituted tetrahydro-β-carboline derivatives via the asymmetric transfer hydrogenation

Roszkowski, Piotr; Wojtasiewicz, Krystyna; Leniewski, Andrzej; Maurin, Jan K.; Lis, Tadeusz; Czarnocki, Zbigniew

doi:10.1016/j.molcata.2005.01.044

Cited by 46 publications

(20 citation statements)

References 23 publications

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“…The absolute configuration of C-1 could not be assigned. Indeed the optical rotation value obtained for 1 was very close to 0 (+4.18) and contradictory information about C-1 stereochemistry were reported for closely related compounds (Chrisey and Brossi, 1990;Reddy and Cook, 1994;Roszkowski et al, 2005;Yan et al, 2013). It was not possible based on literature comparison to deduce unambiguously C-1 stereochemistry and 1 might occur as partial racemic mixture as this was also reported for 1,2,3,4-tetrahydroroeharmine (Reddy and Cook, 1994).…”

Section: Resultsmentioning

confidence: 80%

Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Queiroz

Zeraik

et al. 2014

Phytochemistry Letters

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Section: Resultsmentioning

confidence: 80%

Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Queiroz

Zeraik

et al. 2014

Phytochemistry Letters

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“…Tietze et al used a strategy of oxidizing racemic 1,2,3,4-tetrahydroisoquinolines to the imines, then reducing them with Noyoris catalyst to form chiral versions, in the synthesis of several naturally occurring and novel alkaloids [192,193]. Czarnocki and coworkers have produced several 1,2,3,4-tetrahydro-b-carbolines from this reaction [194], including some tetracyclic examples [195] and the antiworm agent (R)-praziquantel [196].…”

Section: Syntheses Using the Asymmetric Transfer Hydrogenation Of Imimentioning

confidence: 99%

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Church¹,

Andersson²

2010

Chiral Amine Synthesis

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This chapter focuses specifically on the synthesis of amines of the form HNR Ã R 1 , NR Ã R 1 R 2 , and HN(X)R Ã (R Ã ¼ chiral alkyl group; R 1 , R 2 ¼ alkyl or aryl groups; X ¼ heteroatom such as N, S, or P) via the asymmetric hydrogenation of imines, enamines, and iminiums. Thus, we will discuss the formation of amines that have (i) chirality a to the nitrogen, and (ii) no carbonyl group a to nitrogen. Many reported examples of this reaction use substrates with C¼N moieties in a ring, so cyclic amines will receive considerable attention. We will discuss in detail the formation of chiral amines using the asymmetric reduction of aza-aromatic substrates, which has been a popular topic in recent years, and will cover the use of N-carbonyl groups to facilitate this reaction. However, the hydrogenations of nonaromatic a,b-unsaturated amides will not be discussed. Though chiral amides (HN(R Ã )C(O)R 1 ) can be produced highly enantioselectively using these reactions, the sheer number of publications on the topic places it outside the scope of this chapter. These hydrogenations are, however, well covered in a number of existing books and review articles [1]. In addition, we will not cover the related process, reductive amination, which is discussed elsewhere in this book.6.2 Chiral Amines with a Disubstituted Nitrogen Atom, HNR Ã R 1 Direct Asymmetric Hydrogenation of Alkyl-and Aryl-Substituted IminesThough less developed than the analogous reductions of olefins and ketones, the iridium-catalyzed asymmetric hydrogenation of imines (especially N-benzyl and Naryl amines) has received considerable study. It has therefore been the subject of

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“…We have recently communicated that the asymmetric hydrogen transfer process is very effective in the enantioselective synthesis of various fatty acid 1-substituted-tetrahydro--carbolines 76, as illustrated in Scheme 14 [34].…”

Section: Enantioselsctive Reduction Of 34-dihydro--carbolinesmentioning

confidence: 99%

Selected Recent Developments in the Enantioselective Reduction of Imines by Asymmetric Transfer Hydrogenation

Czarnocki¹

2007

MROC

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The asymmetric transfer hydrogenation is a highly versatile tool for the stereoselective reduction of C=O and C=N prochiral groups. Carbonyl compounds have been the most frequently used as the synthetic substrates but imines were much less popular despite their importance as the sources of chiral amines. This review summarizes recent development in a search for more effective ligands and conditions of the reduction procedure. Particularly useful appear the mono-tosylated 1,2-diamines as the chirality inductors in the presence of a mixture of formic acid and triethylamine as a hydrogen source. Also, the structure of the substrates plays very important role. The cyclic endogenous imines usually give highest optical yield of the products.

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Enantioselective synthesis of 1-substituted tetrahydro-β-carboline derivatives via the asymmetric transfer hydrogenation

Cited by 46 publications

References 23 publications

Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Antifungals and acetylcholinesterase inhibitors from the stem bark of Croton heliotropiifolius

Chiral Amines from Transition‐Metal‐Mediated Hydrogenation and Transfer Hydrogenation

Selected Recent Developments in the Enantioselective Reduction of Imines by Asymmetric Transfer Hydrogenation

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