Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

Martín Avalos; Reyes Babiano; Pedro Cintas; Fernando R. Clemente; Ruth Gordillo; José L. Jiménez; Juan C. Palacios; Paul R. Raithby

doi:10.1021/jo991841v

Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

Martín Avalos, Reyes Babiano, Pedro Cintas, Fernando R. Clemente, Ruth Gordillo, José L. Jiménez, Juan C. Palacios, Paul R. Raithby

Department of Chemistry

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

37 Citations (SciVal)

Abstract

A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.

Original language	English
Pages (from-to)	5089-5097
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	65
Issue number	17
DOIs	https://doi.org/10.1021/jo991841v
Publication status	Published - 25 Aug 2000

ASJC Scopus subject areas

Organic Chemistry

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title = "Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes",

abstract = "A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.",

author = "Mart{\'i}n Avalos and Reyes Babiano and Pedro Cintas and Clemente, \{Fernando R.\} and Ruth Gordillo and Jim{\'e}nez, \{Jos{\'e} L.\} and Palacios, \{Juan C.\} and Raithby, \{Paul R.\}",

year = "2000",

month = aug,

day = "25",

doi = "10.1021/jo991841v",

language = "English",

volume = "65",

pages = "5089--5097",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

AU - Avalos, Martín

AU - Babiano, Reyes

AU - Cintas, Pedro

AU - Clemente, Fernando R.

AU - Gordillo, Ruth

AU - Jiménez, José L.

AU - Palacios, Juan C.

AU - Raithby, Paul R.

PY - 2000/8/25

Y1 - 2000/8/25

N2 - A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.

AB - A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.

UR - https://www.scopus.com/pages/publications/0034714413

U2 - 10.1021/jo991841v

DO - 10.1021/jo991841v

M3 - Article

AN - SCOPUS:0034714413

SN - 0022-3263

VL - 65

SP - 5089

EP - 5097

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

Abstract

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