Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole] Scaffold via a Formal [3 + 3] Spiroannulation

Chen, Xiang; Zhang, Junqi; Yin, Shao‐Jie; Li, Haiyan; Zhou, Wenjie; Wang, Xingwang

doi:10.1021/acs.orglett.5b01951

Cited by 52 publications

(16 citation statements)

References 41 publications

(10 reference statements)

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“…Zhou, Wang, and co‐workers realized a formal thio [3+3] spiroannulation between indoline‐2‐thiones 30 with N ‐sulfonylimines 340 by using the quinine‐derived thiourea 438 as the organocatalyst. The reaction generated spiro[thiopyranoindole‐benzoisothiazole] derivatives 694 in high yields and stereoselectivities (Scheme ) . This protocol is a further extension of their strategy presented in Scheme …”

Section: Multifunctional Catalystsmentioning

confidence: 92%

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: 92%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…245 Indole-derived benzamides 423 reacted with 1,3dichloro-5,5-diphenylhydantoin (DCDPH, 424) promoted by the Sharpless ligand LVII, to generate the chloro-spiroindoline 425 in good yield (70-90%) and excellent enantioselectivities (up to 96% ee; Scheme 143). 246 Thioindoles 426 reacted with 1-azadienes 427 via a Michael reaction, promoted by a bifunctional tertiary amine/thiourea catalyst XLIX. This is followed by intramolecular thio-acetal formation, leading to the formation of the spiroindoline derivatives 428 in excellent yields (82-99%), total diastereoselectivity, and good to excellent enantioselectivities (74-99% ee) with excellent substrate scope (Scheme 144).…”

Section: Organocatalytic Methodologies For the Synthesis Of Indolesmentioning

confidence: 99%

New development in the enantioselective synthesis of spiro compounds

et al. 2018

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The enantioselective synthesis of spirocycles has long been pursued by organic chemists. Despite their unique 3D properties and presence in several natural products, the difficulty in their enantioselective synthesis makes them underrepresented in pharmaceutical libraries. Since the first pioneering reports of the enantioselective construction of spirosilanes by Tamao et al., significant effort has been devoted towards the development of new promising asymmetric methodologies. Remarkably, with the advent of organocatalysis, particularly over six years, the reported methodologies for the synthesis of spirocycles have increased exponentially. The aim of this review is to summarize the latest trends and developments in the enantioselective synthesis of spirocompounds during these last six years.

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“…In 2015, Wang, Zhou and co‐workers also documented an enantioselective formal thio[3+3] spiroannulation process of indoline‐2‐thiones 109 to 2d that was driven by the chiral quinine‐derived bifunctional tertiary amine‐thiourea catalyst Cat. 2′ , allowing access to a series of densely functionalized spiro[thiopyranoindole‐benzoisothiazole] heterocycles 110 with a spiro C–N/C–S stereogenic center in high yields with good to excellent diastereo‐ and enantioselectivities (Scheme ) . A positive effect of molecular sieves on the selectivity of the reaction was found.…”

Section: Use Of Cyclic Imines 2 Bearing a 1h‐isoindole Moietymentioning

confidence: 99%

Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

Cheng

Shao

2018

Adv Synth Catal

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Scheme 8. Asymmetric Mannichr eaction of 2-aryl-3H-indol-3-ones 1c with aldehydes and ketones catalyzed by l-proline. Scheme 12. Catalytic asymmetric aza-DAr eaction of 2-aryl-3H-indol-3-ones 1c with 2,4-dienals 34 via trienaminec atalysis. Scheme 18. Enantioselective[ 4 + +2] cycloaddition of ketimines 2a or 2b with allenoate 53a catalyzed by (R)-SITCP Cat. 18. Scheme 34. Bifunctional phosphine Cat. 31-catalyzed stepwise [4+ +2]/[2+ +2] cycloadditions between allene ketones 96 and 2d.

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Asymmetric Construction of Spiro[thiopyranoindole-benzoisothiazole] Scaffold via a Formal [3 + 3] Spiroannulation

Cited by 52 publications

References 41 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

New development in the enantioselective synthesis of spiro compounds

Organocatalytic Asymmetric Transformations Involving the Cyclic Imine Moiety in Indole and Isoindole Related Heterocycles

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