Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity

Yasuhiro Nishiyama; Takehiko Wada; Sadayuki Asaoka; Tadashi Mori; Taylor A. McCarty; Nadine D. Kraut; Frank V. Bright; Yoshihisa Inoue

doi:10.1021/ja801254z

Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity

Yasuhiro Nishiyama, Takehiko Wada, Sadayuki Asaoka, Tadashi Mori, Taylor A. McCarty, Nadine D. Kraut, Frank V. Bright, Yoshihisa Inoue

IMRAM - Division of Organic- and Biomaterials Research

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

21 Citations (Scopus)

Abstract

Diethyl ether added as an entrainer (cosolvent) to near- and supercritical CO₂ significantly enhanced the enantioselectivity of photocyclization of 5,5-diphenyl-4-penten-1-ol sensitized by saccharide naphthalenedicarboxylate to give a cyclization product in enantiomeric excesses much larger than those obtained in conventional organic solvents, revealing the unique features of nc- and sc-CO₂ as well as the critical role of entrainer clustering to the intervening diastereomeric exciplex pair.

Original language	English
Pages (from-to)	7526-7527
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	24
DOIs	https://doi.org/10.1021/ja801254z
Publication status	Published - 2008 Jun 18

Access to Document

10.1021/ja801254z

Cite this

@article{f812eb2c662b4022a837474d8021004b,

title = "Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity",

abstract = "Diethyl ether added as an entrainer (cosolvent) to near- and supercritical CO2 significantly enhanced the enantioselectivity of photocyclization of 5,5-diphenyl-4-penten-1-ol sensitized by saccharide naphthalenedicarboxylate to give a cyclization product in enantiomeric excesses much larger than those obtained in conventional organic solvents, revealing the unique features of nc- and sc-CO2 as well as the critical role of entrainer clustering to the intervening diastereomeric exciplex pair.",

author = "Yasuhiro Nishiyama and Takehiko Wada and Sadayuki Asaoka and Tadashi Mori and McCarty, {Taylor A.} and Kraut, {Nadine D.} and Bright, {Frank V.} and Yoshihisa Inoue",

year = "2008",

month = jun,

day = "18",

doi = "10.1021/ja801254z",

language = "English",

volume = "130",

pages = "7526--7527",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide

T2 - Dramatic enhancement of enantioselectivity

AU - Nishiyama, Yasuhiro

AU - Wada, Takehiko

AU - Asaoka, Sadayuki

AU - Mori, Tadashi

AU - McCarty, Taylor A.

AU - Kraut, Nadine D.

AU - Bright, Frank V.

AU - Inoue, Yoshihisa

PY - 2008/6/18

Y1 - 2008/6/18

N2 - Diethyl ether added as an entrainer (cosolvent) to near- and supercritical CO2 significantly enhanced the enantioselectivity of photocyclization of 5,5-diphenyl-4-penten-1-ol sensitized by saccharide naphthalenedicarboxylate to give a cyclization product in enantiomeric excesses much larger than those obtained in conventional organic solvents, revealing the unique features of nc- and sc-CO2 as well as the critical role of entrainer clustering to the intervening diastereomeric exciplex pair.

AB - Diethyl ether added as an entrainer (cosolvent) to near- and supercritical CO2 significantly enhanced the enantioselectivity of photocyclization of 5,5-diphenyl-4-penten-1-ol sensitized by saccharide naphthalenedicarboxylate to give a cyclization product in enantiomeric excesses much larger than those obtained in conventional organic solvents, revealing the unique features of nc- and sc-CO2 as well as the critical role of entrainer clustering to the intervening diastereomeric exciplex pair.

UR - http://www.scopus.com/inward/record.url?scp=45249106344&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=45249106344&partnerID=8YFLogxK

U2 - 10.1021/ja801254z

DO - 10.1021/ja801254z

M3 - Article

AN - SCOPUS:45249106344

SN - 0002-7863

VL - 130

SP - 7526

EP - 7527

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 24

ER -

Entrainer effect on photochirogenesis in near-and supercritical carbon dioxide: Dramatic enhancement of enantioselectivity

Abstract

Access to Document

Other files and links

Fingerprint

Cite this