Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

Takanori Shibata; Toshifumi Uchiyama; Hiroyuki Hirashima; Kohei Endo

doi:10.1351/PAC-CON-10-09-03

Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

Takanori Shibata^*, Toshifumi Uchiyama, Hiroyuki Hirashima, Kohei Endo

^*Corresponding author for this work

School of Advanced Science and Engineering

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

20 Citations (Scopus)

Abstract

Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.

Original language	English
Pages (from-to)	597-605
Number of pages	9
Journal	Pure and Applied Chemistry
Volume	83
Issue number	3
DOIs	https://doi.org/10.1351/PAC-CON-10-09-03
Publication status	Published - 2011

Keywords

Asymmetric synthesis
Cage compounds
Chirality
Cycloaddition
Enantio- selectivity
Polyaryl compounds
Rhodium
Tetraphenylenes
Triynes

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1351/PAC-CON-10-09-03

Cite this

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title = "Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition",

abstract = "Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.",

keywords = "Asymmetric synthesis, Cage compounds, Chirality, Cycloaddition, Enantio- selectivity, Polyaryl compounds, Rhodium, Tetraphenylenes, Triynes",

author = "Takanori Shibata and Toshifumi Uchiyama and Hiroyuki Hirashima and Kohei Endo",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) (Nos. 19350052 and 22350046) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Takasago International Corp. (BINAP derivatives) and Nippon Chemical Industrial Corp. (QuinoxP*) for the gift of chiral ligands.",

year = "2011",

doi = "10.1351/PAC-CON-10-09-03",

language = "English",

volume = "83",

pages = "597--605",

journal = "Pure and Applied Chemistry",

issn = "0033-4545",

publisher = "IUPAC Secretariat",

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T1 - Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

AU - Shibata, Takanori

AU - Uchiyama, Toshifumi

AU - Hirashima, Hiroyuki

AU - Endo, Kohei

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) (Nos. 19350052 and 22350046) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We thank Takasago International Corp. (BINAP derivatives) and Nippon Chemical Industrial Corp. (QuinoxP*) for the gift of chiral ligands.

PY - 2011

Y1 - 2011

N2 - Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.

AB - Two types of enantioselective [2 + 2 + 2] cycloadditions of triynes using chiral rhodium catalysts are disclosed. The intramolecular reaction of ortho-aminophenol-tethered triynes provides chiral tripodal compounds. Consecutive inter- and intramolecular reactions of ortho-phenylene-tethered triynes provide chiral tetraphenylenes.

KW - Asymmetric synthesis

KW - Cage compounds

KW - Chirality

KW - Cycloaddition

KW - Enantio- selectivity

KW - Polyaryl compounds

KW - Rhodium

KW - Tetraphenylenes

KW - Triynes

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U2 - 10.1351/PAC-CON-10-09-03

DO - 10.1351/PAC-CON-10-09-03

M3 - Article

AN - SCOPUS:79951842433

SN - 0033-4545

VL - 83

SP - 597

EP - 605

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 3

ER -

Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition

Abstract

Keywords

ASJC Scopus subject areas

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