Highly diastereoselective diels-alder reaction mediated by a chiral auxiliary derived from amino indanol: The role of conformation on diastereoselectivity

Davies, Ian W.; Senanayake, Chris H.; Castonguay, Laurie A.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J.

doi:10.1016/0040-4039(95)01584-5

Cited by 59 publications

(17 citation statements)

References 7 publications

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“…Chiral auxiliary derived asymmetricalkylation reactions have been identi�ed as general method for asymmetric carbon-carbon bond formation [15,16]. In this connection, Evans asymmetric strategy is the most powerful synthetic method that has been widely employed in natural product synthesis [17][18][19][20][21][22][23]. Moreover, the Evans type auxiliaries are inexpensive, nontoxic, available in both enantiomeric forms, and already explored for large scale synthesis of pharmaceutical important molecule like "Ezetimibe" (marketed as Zetia or Ezetrol) [24] antihyper lipidemic drug and "Tapentadol" (trade name Nucynta, in India Zyntap) is a centrally acting analgesic [25], and so forth.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Antiepileptic Agent, (−)‐Levetiracetam, through Evans Asymmetric Strategy

Babu

Reddy

Mukkanti

et al. 2012

Journal of Chemistry

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A practical and efficient enantioselective synthesis of antiepileptic drug, (−)-Levetiracetam, has been described in five steps (33.0% overall yield) and high optical purity (99.0%ee), using Evans asymmetric strategy forα-alkylation of carbonyl functionality as the key step. The simplicity of the experimental procedures and high stereochemical outcome make this method synthetically attractive for preparing the target compound on multigram scales.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Antiepileptic Agent, (−)‐Levetiracetam, through Evans Asymmetric Strategy

Babu

Reddy

Mukkanti

et al. 2012

Journal of Chemistry

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“…In the next step, 56 can be chemically converted by addition of acetonitrile in the presence of a strong aqueous acid (Ritter reaction) to give cis-(1S)-amino-(2R)-indanol 57, an important building block of indinavir 58 (Scheme 36.21). [94][95][96] Another important example is the production of indigo 62 from glucose in recombinant E. coli by Genencor International (Palo Alto, CA). 96 The elucidation of indigo's structure in 1883 was followed by the development of a commercially practical synthesis, supplanting in this way the plant-derived product.…”

Section: Rieske Dioxygenasesmentioning

confidence: 99%

Biocatalytic Asymmetric Oxidations in Stereoselective Synthesis

Schallmey

Marı́a

Bracco

2013

Stereoselective Synthesis of Drugs and Natural Products

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Enzyme‐catalyzed oxidations represent a versatile approach for the production of optically active building blocks and natural products. Moreover, enzymatic reaction conditions are often mild and with high atom economy, thus, enabling the basis for future environmentally friendly chemistry. As a result, several biocatalytic oxidative processes have already been implemented on an industrial scale as well, clearly showing that modern biocatalysis can compete economically with other chemical‐based processes. This chapter thoroughly describes the different types of oxidative enzymes that can be found in nature, namely, dehydrogenases, oxygenases, oxidases, and peroxidases, with emphasis on their mechanism and occurrence. Furthermore, several outstanding examples of biocatalytic applications of these enzymes are given—either by means of recombinant whole cells or isolated enzymes—involving the production of different drugs and natural products in which a catalytic step is catalyzed by these oxidative enzymes.

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“…The major compound ( 282 , endo adduct) was isolated with d.r.>99:1 and in 80 % yield after recrystallization of the isolated product from n ‐heptane. Based on precedents at Merck,169 it was assumed that the use of chiral auxiliaries derived from aminoindanol might provide higher levels of stereocontrol than those reported for the Evans‐type oxazolidinone. Indeed, when cyclopentadiene was treated with such a conformationally constrained imide dienophile ( 280 )170 in the presence of Me 2 AlCl, only two diastereomers were obtained, the expected one ( 284 ) being formed in a more favorable ratio of 97.3:2.7.…”

Section: Active Pharmaceutical Ingredientsmentioning

confidence: 99%

Determination of Sudan IV in hot chilli powder with luminol/dissolved oxygen chemiluminescence system

2009

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The proposed method was successfully applied to the determination of Sudan IV in contaminated hot chilli powder, with recoveries ranging from 89.3 to 108.4%. The possible mechanism of enhancement of the luminol/dissolved oxygen CL reaction by Sudan IV can be attributed to the acceleration of electron transfer. Compared with other procedures, the proposed CL method offers the highest sensitivity and the least reagent consumption for the determination of Sudan IV.

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Highly diastereoselective diels-alder reaction mediated by a chiral auxiliary derived from amino indanol: The role of conformation on diastereoselectivity

Cited by 59 publications

References 7 publications

Enantioselective Synthesis of Antiepileptic Agent, (−)‐Levetiracetam, through Evans Asymmetric Strategy

Enantioselective Synthesis of Antiepileptic Agent, (−)‐Levetiracetam, through Evans Asymmetric Strategy

Biocatalytic Asymmetric Oxidations in Stereoselective Synthesis

Determination of Sudan IV in hot chilli powder with luminol/dissolved oxygen chemiluminescence system

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