Enantioselective Alkylation by Binaphthyl Chiral phase-transfer catalysts

A DFT-based conformational analysis

Takashi Kamachi, Kazunari Yoshizawa

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A conformational search method based on the density functional theory (DFT) was successfully applied to explore a mechanism for the highly enantioselective alkylation by binaphthyl-modifed chiral phase-transfer catalysts. Key interactions that govern the enantioselectivity were analyzed. The computational results are encouraging for further application of the DFT-based conformational search toward the rational design of next-generation asymmetric phase transfer catalysts.

Original languageEnglish
Pages (from-to)472-475
Number of pages4
JournalOrganic Letters
Volume16
Issue number2
DOIs
Publication statusPublished - Mar 17 2014

Fingerprint

alkylation
Alkylation
Density functional theory
density functional theory
catalysts
Catalysts
Enantioselectivity
interactions

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Enantioselective Alkylation by Binaphthyl Chiral phase-transfer catalysts : A DFT-based conformational analysis. / Kamachi, Takashi; Yoshizawa, Kazunari.

In: Organic Letters, Vol. 16, No. 2, 17.03.2014, p. 472-475.

Research output: Contribution to journalArticle

@article{88218d2564c04825a20bee17fb767acf,
title = "Enantioselective Alkylation by Binaphthyl Chiral phase-transfer catalysts: A DFT-based conformational analysis",
abstract = "A conformational search method based on the density functional theory (DFT) was successfully applied to explore a mechanism for the highly enantioselective alkylation by binaphthyl-modifed chiral phase-transfer catalysts. Key interactions that govern the enantioselectivity were analyzed. The computational results are encouraging for further application of the DFT-based conformational search toward the rational design of next-generation asymmetric phase transfer catalysts.",
author = "Takashi Kamachi and Kazunari Yoshizawa",
year = "2014",
month = "3",
day = "17",
doi = "10.1021/ol4033545",
language = "English",
volume = "16",
pages = "472--475",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Enantioselective Alkylation by Binaphthyl Chiral phase-transfer catalysts

T2 - A DFT-based conformational analysis

AU - Kamachi, Takashi

AU - Yoshizawa, Kazunari

PY - 2014/3/17

Y1 - 2014/3/17

N2 - A conformational search method based on the density functional theory (DFT) was successfully applied to explore a mechanism for the highly enantioselective alkylation by binaphthyl-modifed chiral phase-transfer catalysts. Key interactions that govern the enantioselectivity were analyzed. The computational results are encouraging for further application of the DFT-based conformational search toward the rational design of next-generation asymmetric phase transfer catalysts.

AB - A conformational search method based on the density functional theory (DFT) was successfully applied to explore a mechanism for the highly enantioselective alkylation by binaphthyl-modifed chiral phase-transfer catalysts. Key interactions that govern the enantioselectivity were analyzed. The computational results are encouraging for further application of the DFT-based conformational search toward the rational design of next-generation asymmetric phase transfer catalysts.

UR - http://www.scopus.com/inward/record.url?scp=84896780645&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84896780645&partnerID=8YFLogxK

U2 - 10.1021/ol4033545

DO - 10.1021/ol4033545

M3 - Article

VL - 16

SP - 472

EP - 475

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 2

ER -