Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization

被引：7

作者：

Ishikawa, Hiroki ^{[1
]}

Uemura, Naohiro ^{[1
]}

Saito, Rei ^{[1
]}

Yoshida, Yasushi ^{[1
,2
]}

Mino, Takashi ^{[1
,2
]}

Kasashima, Yoshio ^{[3
]}

Sakamoto, Masami ^{[1
,2
]}

机构：

[1] Chiba Univ, Grad Sch Engn, Dept Appl Chem & Biotechnol, Inage Ku, Yayoi Cho, Chiba 2638522, Japan

[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, Yayoi Cho, Chiba 2638522, Japan

[3] Chiba Inst Technol, Fac Creat Engn, Educ Ctr, Narashino, Chiba 2750023, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 41期

关键词：

chiral symmetry breaking; deracemization; dynamic crystallization; spirooxazines; spiropyrans; INDUCED ASYMMETRIC TRANSFORMATION; THERMAL RACEMIZATION; RESOLUTION; IMPURITIES; DERACEMIZATION; SUBSTITUENT; GENERALITY; SYSTEMS; FORMS; RULE;

D O I：

10.1002/chem.201901889

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor-diffusion crystallization or attrition-enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single-crystal X-ray analysis and each enantiomorphic crystal was correlated with its solid-state circular dichroism (CD) spectrum.

引用

页码：9758 / 9763

页数：6

共 50 条

[21] SECONDARY NUCLEATION THAT LEADS TO CHIRAL-SYMMETRY BREAKING IN STIRRED CRYSTALLIZATION
KONDEPUDI, DK
SABANAYAGAM, C
[J]. CHEMICAL PHYSICS LETTERS, 1994, 217 (04) : 364 - 368
[22] BREAKING CHIRAL SYMMETRY
GLASHOW, SL
WEINBERG, S
[J]. PHYSICAL REVIEW LETTERS, 1968, 20 (05) : 224 - &
[23] CHIRAL SYMMETRY BREAKING
PAGELS, H
[J]. BULLETIN OF THE AMERICAN PHYSICAL SOCIETY, 1974, 19 (04): : 587 - 587
[24] Spontaneous symmetry breaking and chiral symmetry
Li, LF
[J]. PARTICLES AND FIELDS, 2000, 531 : 16 - 44
[25] Chiral symmetry breaking during crystallization: Complete chiral purity induced by nonlinear autocatalysis and recycling
Viedma, C
[J]. PHYSICAL REVIEW LETTERS, 2005, 94 (06)
[26] FLAVOR MIXING VIA DYNAMIC CHIRAL SYMMETRY-BREAKING
BERNARD, V
JAFFE, RL
MEISSNER, UG
[J]. PHYSICS LETTERS B, 1987, 198 (01) : 92 - 98
[27] A COVARIANT MODEL FOR DYNAMIC CHIRAL-SYMMETRY BREAKING IN QCD
VONSMEKAL, L
AMUNDSEN, PA
ALKOFER, R
[J]. NUCLEAR PHYSICS A, 1991, 529 (04) : 633 - 652
[28] PROPER VERTEX IN STUDIES OF DYNAMIC CHIRAL SYMMETRY-BREAKING
HAWES, FT
WILLIAMS, AG
[J]. PHYSICS LETTERS B, 1991, 268 (02) : 271 - 278
[29] Chiral symmetry breaking in stirred crystallization of 1,1′-binaphthyl melt
Kondepudi, DK
Laudadio, J
Asakura, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (07) : 1448 - 1451
[30] Hydrogen bond induced chiral symmetry breaking in the crystallization of nickel(II) complexes
Guang-Chuan Ou
Zhi-Zhang Li
Lin Yuan
Xian-You Yuan
[J]. Transition Metal Chemistry, 2014, 39 : 393 - 398

← 1 2 3 4 5 →