1990
DOI: 10.1246/cl.1990.1615
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Optically Active O-Acyl Cyanohydrins as Chiral Dopants for Ferroelectric Liquid Crystals

Abstract: O-Acyl cyanohydrins having a chiral center directly connected to the core aromatic ring were prepared through asymmetric hydrocyanation of 4-substituted benzaldehydes and shown to be excellent chiral dopants for ferroelectric liquid crystals.

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Cited by 24 publications
(11 citation statements)
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“…Alternatively, rather than starting from a phenolic mesogen and an optically active alcohol, the synthesis of (R)-1-(4 -nonyloxybiphenyl-4-yl)-4-(1-propoxyethyl)benzoate (101) [149] is based on the enantioselective reduction of a prochiral precursor; this is outlined in Scheme 14.8. The achiral starting material methyl 4-acetylbenzoate (97) was enantioselectively reduced using borane in the presence of the chiral oxazaborolidine (98) (itself synthesized from (S)-(−)-2-diphenylhydroxymethyl)pyrrolidine and BH 3 • THF [150]) to yield the optically active benzyl alcohol (99), in 89% ee.…”
Section: Binary Mixture Studies Involving the Chiral Nematogens (R)-2mentioning
confidence: 99%
See 1 more Smart Citation
“…Alternatively, rather than starting from a phenolic mesogen and an optically active alcohol, the synthesis of (R)-1-(4 -nonyloxybiphenyl-4-yl)-4-(1-propoxyethyl)benzoate (101) [149] is based on the enantioselective reduction of a prochiral precursor; this is outlined in Scheme 14.8. The achiral starting material methyl 4-acetylbenzoate (97) was enantioselectively reduced using borane in the presence of the chiral oxazaborolidine (98) (itself synthesized from (S)-(−)-2-diphenylhydroxymethyl)pyrrolidine and BH 3 • THF [150]) to yield the optically active benzyl alcohol (99), in 89% ee.…”
Section: Binary Mixture Studies Involving the Chiral Nematogens (R)-2mentioning
confidence: 99%
“…The first steps illustrated are the formation of the nonsterol phenolic units; in this case, Schiff's bases, chalcones, and substituted ethynylbenzenes were used to form tolane derivatives. The Schiff's base structures (150) are easily made by condensation reaction of 4-substituted-aminobenzenes (148) and 4-hydroxybenzaldehyde (149). Chalcone-derived units (153) are made by Claisen-Schmidt condensations of 4-substituted benzaldehyde (151) and 4-hydroxyacetophenone (152).…”
Section: Type Iic and D Materials Using One Or Two Chiral Coresmentioning
confidence: 99%
“…Cyanohydrins are valuable intermediates for the synthesis of range of compounds viz., a-amino acids, a-hydroxy acids, b-amino alcohols, vicinal diols and a-hydroxy ketones [1][2][3][4][5] which are important building blocks for numerous pharmaceuticals, agrochemicals and insecticides [6][7][8][9][10][11][12][13]. Cyanohydrins are conventionally synthesized by the cyanation of carbonyl compounds using KCN, NaCN, trimethylsilyl cyanide (TMSCN) and HCN as sources of cyanide in the presence of various Lewis acid/base catalysts [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30].…”
Section: Introductionmentioning
confidence: 99%
“…Cyanohydrins are versatile intermediates, which can easily be converted into wide variety of valuable classes of compounds, such as a-amino acids, a-hydroxy acids, b-amino alcohols, vicinal diols, a-hydroxy ketones [1] for their application in pharmaceuticals, agrochemicals and insecticides [2]. Cyanohydrins are typically prepared by the interaction of carbonyl compound with a cyanide source serving as nucleophile.…”
Section: Introductionmentioning
confidence: 99%