One‐Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols

Dai, Qipu; Arman, Hadi D.; Zhao, Caidan

doi:10.1002/chem.201203104

Cited by 42 publications

(33 citation statements)

References 75 publications

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“…As shown in Scheme , the domino Henry/Michael reaction between 7‐oxohept‐5‐en‐1‐als 541 and nitromethane ( 487 ) catalyzed by the quinidine‐derived thiourea 447 provided a diastereomeric mixture of the desired cyclohexanols ( 542a , 542b , and 542c ) initially. Treatment of this diastereomeric mixture in situ with a catalytic amount of tetramethylguanidine led to the isomerization of the thermodynamically less stable diastereomers 542b and 542c to the thermodynamically more stable diastereomer 542a via a domino retro‐Henry/Henry reaction . Through this sequential catalysis, single diastereomers of 542a were obtained in excellent yields and good to excellent ee values.…”

Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…Zhao and co-workers employed the bifunctional cinchona-derived thiourea 181 to catalyze the tandem Henry–Michael reaction of nitromethane ( 101 ) to the enal 192 , but the reaction resulted in three diastereoisomers ( Scheme 62 ) [ 83 ]. With this in hand, they envisioned the interconversion of the kinetic products to the most stable product.…”

Section: Reviewmentioning

confidence: 99%

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

Koutoulogenis¹,

Kaplaneris²,

Kokotos³

2016

Beilstein J. Org. Chem.

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SummaryOrganocatalysis, now running its second decade of life, is being considered one of the main tools a synthetic chemist has to perform asymmetric catalysis. In this review the synthesis of six-membered rings, that contain multiple chiral centers, either by a ring closing process or by a functionalization reaction on an already existing six-membered ring, utilizing bifunctional (thio)ureas will be summarized. Initially, the use of primary amine-thioureas as organocatalysts for the above transformation is being discussed, followed by the examples employing secondary amine-thioureas. Finally, the use of tertiary amine-thioureas and miscellaneous examples are presented.

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“…Subsequent retro‐Henry/Henry reaction sequence was catalyzed by tetramethyl‐guanidine 206 and yield the functionalized cyclohexanes. The initial Henry/Michael cascade of nitromethane 124 and α,β‐unsaturated keto aldehydes is catalyzed by quinidine derived thiourea 27 (Scheme ) 230. For a cinchona alkaloid catalyzed aza‐Henry/aza‐Michael cascade to access optically active pyrrolidine see reference231.…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

197

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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One‐Pot Sequential Organocatalysis: Highly Stereoselective Synthesis of Trisubstituted Cyclohexanols

Cited by 42 publications

References 75 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

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