Microwave-specific effect on enantioselective reactions

Taichi Sawada, Tohru Yamada

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

Microwave irradiation is widely applied to organic synthesis. Many advantages of microwave irradiation, including drastic shortening of reaction time, suppression of side reactions, and/or higher chemical yield, have been proposed. Generally, these effects have been understood merely as a simple thermal effect, since microwave irradiation rapidly raises the temperature of the reaction mixture. However, some observed results could not be understood only by the thermal effect. Recently our group reported that several enantioselective reactions were accelerated under microwave irradiation without loss of enantioselectivity. As these extraordinary results could not be explained by the simple thermal effect, the concept of the "microwave-specific effect" should be considered. We describe our recent experimental results to elucidate the microwave-specific effect. Investigations are described on enantioselective ring-opening reactions of biaryl lactone derivatives, racemization of an optically pure biaryl lactone derivative, enantioselective Claisen rearrangement reaction, enantioselective Conia-ene reaction and ring-closing metathesis reaction. These reactions or racemization of optically pure compounds were accelerated under microwave conditions. Such reaction acceleration of enantioselective reactions was observed without loss of enantioselectivity.

Original languageEnglish
Pages (from-to)121-128
Number of pages8
JournalJournal of the Japan Petroleum Institute
Volume61
Issue number2
DOIs
Publication statusPublished - 2018 Jan 1

Fingerprint

Microwave irradiation
Microwaves
Thermal effects
Enantioselectivity
Derivatives
Temperature

Keywords

  • Conia-ene reaction
  • Enantioselective reaction
  • Microwave-assisted reaction
  • Microwave-specific effect
  • Ring closing metathesis

ASJC Scopus subject areas

  • Fuel Technology
  • Energy Engineering and Power Technology

Cite this

Microwave-specific effect on enantioselective reactions. / Sawada, Taichi; Yamada, Tohru.

In: Journal of the Japan Petroleum Institute, Vol. 61, No. 2, 01.01.2018, p. 121-128.

Research output: Contribution to journalReview article

@article{12e1ec03e74f45beae2c3b8f0b544a61,
title = "Microwave-specific effect on enantioselective reactions",
abstract = "Microwave irradiation is widely applied to organic synthesis. Many advantages of microwave irradiation, including drastic shortening of reaction time, suppression of side reactions, and/or higher chemical yield, have been proposed. Generally, these effects have been understood merely as a simple thermal effect, since microwave irradiation rapidly raises the temperature of the reaction mixture. However, some observed results could not be understood only by the thermal effect. Recently our group reported that several enantioselective reactions were accelerated under microwave irradiation without loss of enantioselectivity. As these extraordinary results could not be explained by the simple thermal effect, the concept of the {"}microwave-specific effect{"} should be considered. We describe our recent experimental results to elucidate the microwave-specific effect. Investigations are described on enantioselective ring-opening reactions of biaryl lactone derivatives, racemization of an optically pure biaryl lactone derivative, enantioselective Claisen rearrangement reaction, enantioselective Conia-ene reaction and ring-closing metathesis reaction. These reactions or racemization of optically pure compounds were accelerated under microwave conditions. Such reaction acceleration of enantioselective reactions was observed without loss of enantioselectivity.",
keywords = "Conia-ene reaction, Enantioselective reaction, Microwave-assisted reaction, Microwave-specific effect, Ring closing metathesis",
author = "Taichi Sawada and Tohru Yamada",
year = "2018",
month = "1",
day = "1",
doi = "10.1627/jpi.61.121",
language = "English",
volume = "61",
pages = "121--128",
journal = "Journal of the Japan Petroleum Institute",
issn = "1346-8804",
publisher = "Japan Petroleum Institute",
number = "2",

}

TY - JOUR

T1 - Microwave-specific effect on enantioselective reactions

AU - Sawada, Taichi

AU - Yamada, Tohru

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Microwave irradiation is widely applied to organic synthesis. Many advantages of microwave irradiation, including drastic shortening of reaction time, suppression of side reactions, and/or higher chemical yield, have been proposed. Generally, these effects have been understood merely as a simple thermal effect, since microwave irradiation rapidly raises the temperature of the reaction mixture. However, some observed results could not be understood only by the thermal effect. Recently our group reported that several enantioselective reactions were accelerated under microwave irradiation without loss of enantioselectivity. As these extraordinary results could not be explained by the simple thermal effect, the concept of the "microwave-specific effect" should be considered. We describe our recent experimental results to elucidate the microwave-specific effect. Investigations are described on enantioselective ring-opening reactions of biaryl lactone derivatives, racemization of an optically pure biaryl lactone derivative, enantioselective Claisen rearrangement reaction, enantioselective Conia-ene reaction and ring-closing metathesis reaction. These reactions or racemization of optically pure compounds were accelerated under microwave conditions. Such reaction acceleration of enantioselective reactions was observed without loss of enantioselectivity.

AB - Microwave irradiation is widely applied to organic synthesis. Many advantages of microwave irradiation, including drastic shortening of reaction time, suppression of side reactions, and/or higher chemical yield, have been proposed. Generally, these effects have been understood merely as a simple thermal effect, since microwave irradiation rapidly raises the temperature of the reaction mixture. However, some observed results could not be understood only by the thermal effect. Recently our group reported that several enantioselective reactions were accelerated under microwave irradiation without loss of enantioselectivity. As these extraordinary results could not be explained by the simple thermal effect, the concept of the "microwave-specific effect" should be considered. We describe our recent experimental results to elucidate the microwave-specific effect. Investigations are described on enantioselective ring-opening reactions of biaryl lactone derivatives, racemization of an optically pure biaryl lactone derivative, enantioselective Claisen rearrangement reaction, enantioselective Conia-ene reaction and ring-closing metathesis reaction. These reactions or racemization of optically pure compounds were accelerated under microwave conditions. Such reaction acceleration of enantioselective reactions was observed without loss of enantioselectivity.

KW - Conia-ene reaction

KW - Enantioselective reaction

KW - Microwave-assisted reaction

KW - Microwave-specific effect

KW - Ring closing metathesis

UR - http://www.scopus.com/inward/record.url?scp=85043511891&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85043511891&partnerID=8YFLogxK

U2 - 10.1627/jpi.61.121

DO - 10.1627/jpi.61.121

M3 - Review article

AN - SCOPUS:85043511891

VL - 61

SP - 121

EP - 128

JO - Journal of the Japan Petroleum Institute

JF - Journal of the Japan Petroleum Institute

SN - 1346-8804

IS - 2

ER -