Keywords
conglomerates
enantiomers
lamellar twinning
preferencial crystallization
racemates
spontaneous resolution
Abstract
The 100-year history of this unusual crystalline form of organic racemates resulted so far in only nineteen (19!) examples, among which amino acids, helicenes, and one steroid are presented. It is expected that such lamellar conglomerates (LC) are much more numerous. The review provides a comparison of the properties of LC and plain conglomerates as a basis for the search of new LC, and describes the prospects of the practical LC application in enantioselective synthesis.
References
1.
10.1016/j.mencom.2020.01.001_bib0005
Jacques
Enantiomers, Racemates and Resolutions,
1994
2.
10.1016/j.mencom.2020.01.001_bib0010
Eliel
Stereochemistry of Organic Compounds,
1994
3.
Lorenz H., Seidel-Morgenstern A.
Angewandte Chemie - International Edition,
2014
4.
Gonella S., Mahieux J., Sanselme M., Coquerel G.
Organic Process Research and Development,
2011
5.
Otero-de-la-Roza A., Hein J.E., Johnson E.R.
Crystal Growth and Design,
2016
6.
Collet A., Brienne M.J., Jacques J.
Chemical Reviews,
1980
7.
Alvarez Rodrigo A., Lorenz H., Seidel-Morgenstern A.
Chirality,
2004
8.
Polenske D., Lorenz H., Seidel-Morgenstern A.
Chirality,
2009
9.
10.1016/j.mencom.2020.01.001_bib0025
Coquerel
Top. Curr. Chem.,
2007
10.
Levilain G., Coquerel G.
CrystEngComm,
2010
11.
Kislyi V.P., Zubavichus Y.V., Babievsky K.K., Khrustalev V.N., Pivnitsky K.K.
Mendeleev Communications,
2019
12.
Lamellar Twinning Explains the Nearly Racemic Composition of Chiral, Single Crystals of Hexahelicene
Green B.S., Knossow M.
Science,
1981
13.
Gervais C., Beilles S., Cardinaël P., Petit S., Coquerel G.
Journal of Physical Chemistry B,
2001
14.
Torbeev V.Y., Lyssenko K.A., Kharybin O.N., Antipin M.Y., Kostyanovsky R.G.
Journal of Physical Chemistry B,
2003
15.
Riiber C.N.
Berichte der deutschen chemischen Gesellschaft,
1915
16.
10.1016/j.mencom.2020.01.001_sbref0055b
Goldschmidt
Z. Krist.,
1915
17.
Furberg S., Hassel O., Webb M., Rottenberg M.
Acta Chemica Scandinavica,
1950
18.
Martin R.H., Flammang-Barbieux M., Cosyn J.P., Gelbcke M.
Tetrahedron Letters,
1968
19.
Martin R.H., Marchant M.J.
Tetrahedron,
1974
20.
Addadi L., Weinstein S., Gati E., Weissbuch I., Lahav M.
Journal of the American Chemical Society,
1982
21.
Potter G.A., Garcia C., McCague R., Adger B., Collet A.
1996
22.
Berfeld M., Zbaida D., Leiserowitz L., Lahav M.
Advanced Materials,
1999
23.
Zbaida D., Lahav M., Drauz K., Knaup G., Kottenhahn M.
Tetrahedron,
2000
24.
Weissbuch I., Lahav M., Leiserowitz L.
Crystal Growth and Design,
2003
25.
Beilles S., Cardinael P., Ndzié E., Petit S., Coquerel G.
Chemical Engineering Science,
2001
26.
Kostyanovsky R.G., Lyssenko K.A., Kravchenko A.N., Lebedev O.V., Kadorkina G.K., Kostyanovsky V.R.
Mendeleev Communications,
2001
27.
10.1016/j.mencom.2020.01.001_sbref0100b
Pletnev
Russ. J. Bioorg. Chem.,
1993
28.
Kaptein B., Noorduin W., Meekes H., van Enckevort W. ., Kellogg R., Vlieg E.
Angewandte Chemie - International Edition,
2008
29.
van Eupen J.T., Elffrink W.W., Keltjens R., Bennema P., de Gelder R., Smits J.M., van Eck E.R., Kentgens A.P., Deij M.A., Meekes H., Vlieg E.
Crystal Growth and Design,
2008
30.
Mahieux J., Sanselme M., Harthong S., Melan C., Aronica C., Guy L., Coquerel G.
Crystal Growth and Design,
2013
31.
Black S.N., Williams L.J., Davey R.J., Moffatt F., Jones R.V., McEwan D.M., Sadler D.E.
Tetrahedron,
1989
32.
Black S.N., Williams L.J., Davey R.J., Moffatt F., McEwan D.M., Sadler D.E., Docherty R., Williams D.J.
The Journal of Physical Chemistry,
1990
33.
Davey R.J., Black S.N., Williams L.J., McEwan D., Sadler D.E.
Journal of Crystal Growth,
1990
34.
Levilain G., Rougeot C., Guillen F., Plaquevent J., Coquerel G.
Tetrahedron Asymmetry,
2009
35.
Suwannasang K., Flood A.E., Rougeot C., Coquerel G.
Crystal Growth and Design,
2013
36.
Davey R.J., Sadiq G., Seaton C.C., Pritchard R.G., Coquerel G., Rougeot C.
CrystEngComm,
2014
37.
Mbodji A., Gbabode G., Sanselme M., Couvrat N., Leeman M., Dupray V., Kellogg R.M., Coquerel G.
Crystal Growth and Design,
2019
38.
39.
10.1016/j.mencom.2020.01.001_sbref0140b
Wederpohl
Naturwissenschaften,
1996
40.
Levkin P.A., Torbeev V.Y., Lenev D.A., Kostyanovsky R.G.
Topics in Stereochemistry,
2006
41.
van Enckevort W.J.
Journal of Physical Chemistry C,
2010
42.
D’Oria E., Karamertzanis P.G., Price S.L.
Crystal Growth and Design,
2010
43.
Gavezzotti A., Rizzato S.
Journal of Organic Chemistry,
2014