Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction

Chandra S. Azad; Pratibha Shukla; Mark A. Olson; Anudeep K. Narula

doi:10.1002/cjoc.202000634

Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction

Chandra S. Azad, Pratibha Shukla, Mark A. Olson^*, Anudeep K. Narula

^*Corresponding author for this work

Chemistry

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

1 Scopus citations

Abstract

A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach. This new and quite mild catalytic system, comprised of phenylphosphinic acid/NaI, was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.

Original language	English (US)
Pages (from-to)	1503-1510
Number of pages	8
Journal	Chinese Journal of Chemistry
Volume	39
Issue number	6
DOIs	https://doi.org/10.1002/cjoc.202000634
State	Published - Jun 2021

Funding

CSA acknowledges the Tianjin University for the financial assistance. PS acknowledges the GGS IP Universality for financial assistance and TRC lab for analytical data.

Keywords

Azasugars
Isocyanide
Multicomponent reactions
Nitrilium ion
Reductivecyclization

ASJC Scopus subject areas

General Chemistry

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10.1002/cjoc.202000634

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title = "Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction",

abstract = "A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach. This new and quite mild catalytic system, comprised of phenylphosphinic acid/NaI, was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.",

keywords = "Azasugars, Isocyanide, Multicomponent reactions, Nitrilium ion, Reductivecyclization",

author = "Azad, \{Chandra S.\} and Pratibha Shukla and Olson, \{Mark A.\} and Narula, \{Anudeep K.\}",

note = "Funding Information: CSA acknowledges the Tianjin University for the financial assistance. PS acknowledges the GGS IP Universality for financial assistance and TRC lab for analytical data. Publisher Copyright: {\textcopyright} 2021 SIOC, CAS, Shanghai and Wiley-VCH GmbH",

year = "2021",

month = jun,

doi = "10.1002/cjoc.202000634",

language = "English (US)",

volume = "39",

pages = "1503--1510",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

publisher = "John Wiley and Sons Inc.",

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T1 - Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction

AU - Azad, Chandra S.

AU - Shukla, Pratibha

AU - Olson, Mark A.

AU - Narula, Anudeep K.

N1 - Funding Information: CSA acknowledges the Tianjin University for the financial assistance. PS acknowledges the GGS IP Universality for financial assistance and TRC lab for analytical data. Publisher Copyright: © 2021 SIOC, CAS, Shanghai and Wiley-VCH GmbH

PY - 2021/6

Y1 - 2021/6

N2 - A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach. This new and quite mild catalytic system, comprised of phenylphosphinic acid/NaI, was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.

AB - A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach. This new and quite mild catalytic system, comprised of phenylphosphinic acid/NaI, was used to synthesize both the L-allo-DNJ and L-altro-DNJ in high yield.

KW - Azasugars

KW - Isocyanide

KW - Multicomponent reactions

KW - Nitrilium ion

KW - Reductivecyclization

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DO - 10.1002/cjoc.202000634

M3 - Article

AN - SCOPUS:85105676254

SN - 1001-604X

VL - 39

SP - 1503

EP - 1510

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 6

ER -

Phosphinic Acid/NaI Mediated Reductive Cyclization Approach for Accessing the L-1-Deoxynojirimycin Using a Two-Component Three-Centered (2C3C) Ugi Type Reaction

Abstract

Funding

Keywords

ASJC Scopus subject areas

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