Chemistry Phase-Transfer Catalysts Chiral Phase-Transfer Catalysts

Chiral Phase-Transfer Catalysts

Chiral phase-transfer catalysts (CPTCs) are a class of asymmetric catalysts that enable enantioselective transformations under biphasic or heterogeneous conditions. These catalysts typically consist of chiral quaternary ammonium or phosphonium salts derived from natural products such as Cinchona alkaloids. The chiral environment around the ionic center allows for enantioselective transfer of anions—such as enolates, carbanions, or cyanide ions—into the organic phase, where reactions occur with high enantiocontrol. CPTCs have been applied to a wide variety of asymmetric reactions including alkylations, Michael additions, epoxidations, and aziridinations. Notable examples include the asymmetric alkylation of glycine Schiff bases and the enantioselective Darzens and Mannich-type reactions. Their utility lies in their ability to mediate reactions under mild conditions without requiring metal complexes or inert atmospheres. Chiral phase-transfer catalysis is particularly attractive for industrial applications due to its scalability, low catalyst loadings, and compatibility with green chemistry practices. These catalysts continue to expand the frontiers of asymmetric synthesis in both academic and commercial settings.
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(1S,2S,4S,5R)-1-(Anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride

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A1006252199588-80-285%

(1S,2S,4S,5R)-1-(Anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride

$160.00/100mg

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(11bR)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide

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A1158790887938-70-798%

(11bR)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide

$177.00/25mg

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(11bS)-4,4-Dibutyl-4,5-dihydro-2,6-bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c:1′,2′-e]azepinium bromide

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A517641851942-89-797%

(11bS)-4,4-Dibutyl-4,5-dihydro-2,6-bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c:1′,2′-e]azepinium bromide

$1330.00/250mg

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(11bS)-2,6-Di([1,1':3',1''-terphenyl]-5'-yl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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A1517134862299-29-495%

(11bS)-2,6-Di([1,1':3',1''-terphenyl]-5'-yl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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(11bR,11'bR)-2,6-Bis(3,4,5-trifluorophenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1372019534570-50-898+%

(11bR,11'bR)-2,6-Bis(3,4,5-trifluorophenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(11bS,11'bS)-2,6-Bis(3,4,5-trifluorophenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A559536287384-12-798+%

(11bS,11'bS)-2,6-Bis(3,4,5-trifluorophenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(11bS,11bS)-2,6-Bis(3,3'',5,5''-tetra-tert-butyl-[1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517125501934-21-095%

(11bS,11bS)-2,6-Bis(3,3'',5,5''-tetra-tert-butyl-[1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(S)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-di-tert-butyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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A1517137N/A95%

(S)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-di-tert-butyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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(11bR,11bR)-2,6-Di(naphthalen-2-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517133466679-91-495%

(11bR,11bR)-2,6-Di(naphthalen-2-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(R)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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A1517141N/A95%

(R)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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(R)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-di-tert-butyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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A1517138N/A95%

(R)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-di-tert-butyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin-4-ium bromide

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(11bS,11bS)-2,6-Di(naphthalen-2-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517132237762-42-495%

(11bS,11bS)-2,6-Di(naphthalen-2-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(R)-4,4-Dibutyl-2,6-di(naphthalen-2-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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A1517150N/A95%

(R)-4,4-Dibutyl-2,6-di(naphthalen-2-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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(11bS)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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A1517139862299-31-895%

(11bS)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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(11bR)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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A15171401065472-68-595%

(11bR)-2,6-Bis(3,5-bis(trifluoromethyl)phenyl)-4,4-dibutyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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(11bR,11bR)-2,6-Bis(3,5-di-tert-butylphenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517131724425-22-395%

(11bR,11bR)-2,6-Bis(3,5-di-tert-butylphenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(11bR,11bR)-2,6-Bis(3,3'',5,5''-tetra-tert-butyl-[1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517126534576-68-695%

(11bR,11bR)-2,6-Bis(3,3'',5,5''-tetra-tert-butyl-[1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(S)-4,4-Dibutyl-2,6-di(naphthalen-2-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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A1517149N/A95%

(S)-4,4-Dibutyl-2,6-di(naphthalen-2-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide

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(11bS,11bS)-2,6-Bis(3,5-di-tert-butylphenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517130501934-20-995%

(11bS,11bS)-2,6-Bis(3,5-di-tert-butylphenyl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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(11bS,11bS)-2,6-Di([1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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A1517127534570-44-095%

(11bS,11bS)-2,6-Di([1,1':3',1''-terphenyl]-5'-yl)-3,3',5,5'-tetrahydro-4,4'-spirobi[dinaphtho[2,1-c:1',2'-e]azepin]-4-ium bromide

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