Chirality Transfer during the [2,3]-sila-Wittig Rearrangement and Cyclopropanation Reaction of Optically Active [(sec-Allyloxy)silyl]lithiums

2001 ◽  
Vol 123 (13) ◽  
pp. 3143-3144 ◽  
Author(s):  
Atsushi Kawachi ◽  
Hirofumi Maeda ◽  
Hiroshi Nakamura ◽  
Noriyuki Doi ◽  
Kohei Tamao
Keyword(s):  
Optically Active ◽  
Chirality Transfer ◽  
Wittig Rearrangement

ChemInform Abstract: Chirality Transfer During the [2,3]-Sila-Wittig Rearrangement and Cyclopropanation Reaction of Optically Active [(sec-Allyloxy)silyl]lithiums.

ChemInform ◽  
2010 ◽  
Vol 32 (27) ◽  
pp. no-no
Author(s):  
Atsushi Kawachi ◽  
Hirofumi Maeda ◽  
Hiroshi Nakamura ◽  
Noriyuki Doi ◽  
Kohei Tamao
Keyword(s):  
Optically Active ◽  
Chirality Transfer ◽  
Wittig Rearrangement

ChemInform Abstract: Synthesis of Optically Active Aldol Derivatives Through Chirality Transfer Type 1,2-Wittig Rearrangement of α-Alkoxycarboxamides.

ChemInform ◽  
2010 ◽  
Vol 32 (41) ◽  
pp. no-no
Author(s):  
Osamu Kitagawa ◽  
Shu-ichi Momose ◽  
Yoichiro Yamada ◽  
Motoo Shiro ◽  
Takeo Taguchi
Keyword(s):  
Optically Active ◽  
Chirality Transfer ◽  
Wittig Rearrangement

Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides

2001 ◽  
Vol 42 (29) ◽  
pp. 4865-4868 ◽  
Author(s):  
Osamu Kitagawa ◽  
Shu-ichi Momose ◽  
Yoichiro Yamada ◽  
Motoo Shiro ◽  
Takeo Taguchi
Keyword(s):  
Optically Active ◽  
Chirality Transfer ◽  
Wittig Rearrangement

Central–axial–central chirality transfer: asymmetric synthesis of highly substituted indenes bearing a stereogenic quaternary carbon center from optically active propargyl alcohols

2015 ◽  
Vol 51 (2) ◽  
pp. 380-383 ◽  
Author(s):  
Masahiro Egi ◽  
Kaori Shimizu ◽  
Marin Kamiya ◽  
Yuya Ota ◽  
Shuji Akai
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Quaternary Carbon ◽  
Chirality Transfer ◽  
Propargyl Alcohols

An asymmetric synthesis of highly substituted indenes has been developed via the central–axial–central chirality transfer from optically active propargyl alcohols.

scholarly journals Trityl-Containing Alcohols—An Efficient Chirality Transmission Process from Inductor to the Stereodynamic Propeller and their Solid-State Structural Diversity

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 707 ◽  
Author(s):  
Sylwia Górczyńska ◽  
Aleksandra Brzdonkiewicz ◽  
Maciej Jelecki ◽  
Agnieszka Czapik ◽  
Bartosz Stasiak ◽  
...  
Keyword(s):  
Crystal Engineering ◽  
Electrostatic Interactions ◽  
Structural Diversity ◽  
Optically Active ◽  
Cascade Process ◽  
Chirality Transfer ◽  
Transmission Process ◽  
Close Proximity ◽  
Cotton Effects ◽  
Stereogenic Center

The cascade process of a dynamic chirality transmission from the permanent chirality center to the stereodynamic triphenylmethyl group has been studied for series of optically active trityl derivatives. The structural analysis, carried out with the use of complementary methods, enabled us to determine the mechanism of chirality transfer. The process of chirality transmission involves a set of weak but complementary electrostatic interactions. The induction of helicity in a trityl propeller is revealed by rising non-zero cotton effects in the area of trityl UV-absorption. The presence of an additional stereogenic center in close proximity to the trityl-containing stereogenic center significantly affects the sign and, to a lesser extent, magnitude of the respective cotton effects. Despite the bulkiness of the trityl, in the crystalline phase, the molecules under study strictly fill the space. In the crystal, molecules form aggregates stabilized by OH•••O hydrogen bonds. However, the presence of two trityl groups precludes formation of OH•••O hydrogen bonding. Additionally, the trityl group seems to be responsible for the formation of the solid solutions by e.g., racemates of trans- and cis-2-tritylcyclohexanol. Therefore, the trityl group acts as a supramolecular protective group, which in turn can be used in the crystal engineering.

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