Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization

Zhang, Zhiguo; Song, Xiaoqing; Li, Guofeng; Li, Xiang; Zheng, Dan; Zhao, Xüna; Miao, Huanran; Zhang, Guisheng; Liu, Lantao

doi:10.1016/j.cclet.2020.11.001

Cited by 39 publications

(10 citation statements)

References 57 publications

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“…An IBX-mediated intramolecular cyclization of tryptophan derivatives provided oxazine-containing polycyclic spiro-fused indolines in good diastereoselectivity (Scheme ). A 3:1 mixture of HFIP/H 2 O provided the best yields, however, no reaction was obtained in HFIP or water alone. Replacement of HFIP with TFE, TFP, or OFP provided significantly lower yields.…”

Section: Hypervalent Iodine Chemistrymentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: Hypervalent Iodine Chemistrymentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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“…Zhinguo Zhang and co-researchers investigated on the IBX-mediated intramolecular cascade cyclization reaction of tryptophan analogs bearing the N-aryl amides 81) side chain resulting in the formation of polycyclic spiro-fused indoline scaffolds 82), with multiple stereocenters including quaternary stereocenters ( Supplementary Figure S32 ) ( Zhang et al, 2020 ). Authors claim that this tandem spiro-fused cyclization exhibits highly efficient construction of two stereocenters in one step, including one quaternary carbon stereocenter containing five to eight rings, aiming at structurally diverse oxazine-containing complex polycyclic indolines.…”

Section: Applications Of Ibx In the Synthesis Of Heterocyclesmentioning

confidence: 99%

IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update

Nageswar

Ramesh

2022

Front. Chem.

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“…3) spiroindolines in fair to excellent yeild under mild reaction conditions. [115,116] The phthalamide protecting group prevents competitive primary amide formation. Hexafluoroisopropanol (HFIPA):water in a 3 : 1 ratio was determined as the optimised solvent system, while control experiments in pure HFIPA or aqueous solution returned starting material; which allowed Zhang et al to infer that water microscopically involves in the reaction.…”

Section: Pyrrole or Pyridine From N-hydroxyalkyl Enaminementioning

confidence: 99%

The Mechanistic Perspective of I^V Iodoxolones

Chipman

2021

Asian J Org Chem

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The historical development of ortho-iodoxybenzoic acid (IBX) and the Dess-Martin periodinane (DMP) is précised to introduce a comprehensive catalogue of the plausible reaction mechanisms that have been proposed to explain their organic chemistry. Each example sourced from the I V iodoxolone mechanistic literature is concisely discussed with reference to relevant structures, presented in the format of a chemical reaction diagram. Where apt, electron pushing arrow annotations systematically inspect electron redistributions typically associated with proton migration assisted bond formation or rupture. Along the journey, reviewing the many facetted repertoire of oxidations that can be accessed by an I V iodoxolone reagent, provides critical insight into the versatility and applications of the mild oxidant(s), the underlying organic chemistry, as well as acknowledgment for the scientists who have unpacked the cornucopia of I V iodoxolone chemistry. A narrative is extolled of a how following the intrinsic reaction coordinate (IRC) using density functional theory (DFT) elucidated the general mechanism of IBX mediated primary (1°) alcohol or 1°amine oxidation, which had previously been the subject of a robust interdisciplinary debate within the chemistry community, as to whether proton abstraction or isomerisation represents the rate determining step.

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Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization

Cited by 39 publications

References 57 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update

The Mechanistic Perspective of I^V Iodoxolones

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Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization

Cited by 39 publications

References 57 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update

The Mechanistic Perspective of IV Iodoxolones

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The Mechanistic Perspective of I^V Iodoxolones