One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

Peng Wei Xu; Chen Chen; Jia Kuan Liu; Yu Ting Song; Feng Zhou; Jun Yan; Jian Zhou

doi:10.1021/acs.joc.8b02208

One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

Peng Wei Xu
, Chen Chen
, Jia Kuan Liu
, Yu Ting Song
, Feng Zhou
, Jun Yan^*
, Jian Zhou

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

A Sc(OTf)₃-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxindole-tetrahydro-1,2-oxazines with sufficient structural diversity. The corresponding catalytic enantioselective one-pot protocol of aldehydes is also reported, affording the desired adducts in up to 97% ee. The biological evaluation of selected oxindole-based spirocyclic tetrahydro-1,2-oxazines revealed that they exerted cytotoxic effects on human prostate cancer cells with the capacity to inhibit NFÎ°B signaling in prostate cancer cells.

Original language	English
Pages (from-to)	12763-12774
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	83
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.8b02208
State	Published - 19 Oct 2018
Externally published	Yes

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10.1021/acs.joc.8b02208

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title = "One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole",

abstract = "A Sc(OTf)3-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxindole-tetrahydro-1,2-oxazines with sufficient structural diversity. The corresponding catalytic enantioselective one-pot protocol of aldehydes is also reported, affording the desired adducts in up to 97\% ee. The biological evaluation of selected oxindole-based spirocyclic tetrahydro-1,2-oxazines revealed that they exerted cytotoxic effects on human prostate cancer cells with the capacity to inhibit NF{\^I}°B signaling in prostate cancer cells.",

author = "Xu, \{Peng Wei\} and Chen Chen and Liu, \{Jia Kuan\} and Song, \{Yu Ting\} and Feng Zhou and Jun Yan and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = oct,

day = "19",

doi = "10.1021/acs.joc.8b02208",

language = "英语",

volume = "83",

pages = "12763--12774",

journal = "Journal of Organic Chemistry",

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}

TY - JOUR

T1 - One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

AU - Xu, Peng Wei

AU - Chen, Chen

AU - Liu, Jia Kuan

AU - Song, Yu Ting

AU - Zhou, Feng

AU - Yan, Jun

AU - Zhou, Jian

PY - 2018/10/19

Y1 - 2018/10/19

N2 - A Sc(OTf)3-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxindole-tetrahydro-1,2-oxazines with sufficient structural diversity. The corresponding catalytic enantioselective one-pot protocol of aldehydes is also reported, affording the desired adducts in up to 97% ee. The biological evaluation of selected oxindole-based spirocyclic tetrahydro-1,2-oxazines revealed that they exerted cytotoxic effects on human prostate cancer cells with the capacity to inhibit NFÎ°B signaling in prostate cancer cells.

AB - A Sc(OTf)3-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxindole-tetrahydro-1,2-oxazines with sufficient structural diversity. The corresponding catalytic enantioselective one-pot protocol of aldehydes is also reported, affording the desired adducts in up to 97% ee. The biological evaluation of selected oxindole-based spirocyclic tetrahydro-1,2-oxazines revealed that they exerted cytotoxic effects on human prostate cancer cells with the capacity to inhibit NFÎ°B signaling in prostate cancer cells.

UR - https://www.scopus.com/pages/publications/85054643400

U2 - 10.1021/acs.joc.8b02208

DO - 10.1021/acs.joc.8b02208

M3 - 文章

C2 - 30240218

AN - SCOPUS:85054643400

SN - 0022-3263

VL - 83

SP - 12763

EP - 12774

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

Abstract

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