TCI | Product Information : Synthetic Organic Chemistry Asymmetric Organocatalysts

Asymmetric Organocatalysts

Eder et al. and Hajos et al. separately reported an intramolecular asymmetric aldol reaction which employed proline as the only asymmetric catalyst at the beginning of the 1970s.¹⁾ This reaction was considered to be a special case at that time. Later in 2000, List et al. reported an intermolecular asymmetric aldol reaction which used proline as a catalyst.²⁾ List’s report received broad attention and served as a trigger to make research active for asymmetric organic catalysts. Therefore, varieties of asymmetric organic catalysts have been developed and the research has been applied to many areas.³⁾ The proline derivative 1, having the heterocyclic ring was developed by Nakamura et al. It shows high TON as an asymmetric catalyst for obtaining a chiral aldol adduct.⁴⁾

Compared with conventional metal complex catalysts, asymmetric organic catalysts are considered to be environmentally friendly and are expected to be further developed because they are stable, easy to handle and free of harmful metals.

Prolines and its analogs

D3185	D3186	D3803
D2365	H0784	M1169
P1241	A0945	H0768
M1097	M1183	D3804
A1301	D2735	I0395
M1161	M1995	P1784
M2077	P1830	P0994
A1043	P1404	P0481
T0219	T2637	B3440

D3185	(2R,5R)-2,5-Diphenylpyrrolidine
D3186	(2S,5S)-2,5-Diphenylpyrrolidine
D3803	(R)-(+)-2-(Diphenylmethyl)pyrrolidine
D2365	(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol
H0784	(R)-(-)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine
M1169	(R)-2-(Methoxymethyl)pyrrolidine
P1241	(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine
A0945	(S)-(+)-2-(Anilinomethyl)pyrrolidine
H0768	(S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine
M1097	(S)-(-)-1-Methyl-2-(1-naphthylaminomethyl)pyrrolidine
M1183	(S)-(-)-1-Methyl-2-(1-piperidinomethyl)pyrrolidine
D3804	(S)-(-)-2-(Diphenylmethyl)pyrrolidine
A1301	(S)-(-)-2-Aminomethyl-1-ethylpyrrolidine
D2735	(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol
I0395	(S)-(-)-Indoline-2-carboxylic Acid
M1161	(S)-2-(Methoxymethyl)pyrrolidine
M1995	(S)-2-[(1-Methyl-2-pyrrolidinyl)methyl]isoindoline Dihydrochloride
P1784	(S)-5-(Pyrrolidin-2-yl)-1H-tetrazole
M2077	alpha-Methyl-L-proline
P1830	D-Pipecolic Acid
P0994	D-Proline
A1043	L-Azetidine-2-carboxylic Acid [Antagonist of L-Proline]
P1404	L-Pipecolic Acid
P0481	L-Proline
T0219	L-Thioproline
T2637	N-(2-Thiophenesulfonyl)-L-prolinamide Trifluoroacetate
B3440	trans-4-(tert-Butyldiphenylsilyloxy)-L-proline

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Other Amino Acids

T0228	A0177	T0539
T0230	A0179	T0541
B3398

T0228	D-(+)-Threonine
A0177	D-Alanine
T0539	D-Tryptophan
T0230	L-(-)-Threonine
A0179	L-Alanine
T0541	L-Tryptophan
B3398	O-tert-Butyl-L-threonine

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Cinchona Alkaloids

I0728	beta-Isocupreidine
C0347	Cinchonidine
C0348	Cinchonidine Dihydrochloride
C0349	Cinchonidine Sulfate
C0350	Cinchonine
C0351	Cinchonine Hydrochloride Hydrate
H0752	Hydroquinidine Hydrochloride
B1683	N-Benzylcinchonidinium Chloride [Chiral Phase-Transfer Catalyst]
B1689	N-Benzylcinchoninium Chloride [Chiral Phase-Transfer Catalyst]
B1684	N-Benzylquinidinium Chloride [Chiral Phase-Transfer Catalyst]
B1685	N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst]
Q0076	Quincoridine
Q0074	Quincorine
Q0006	Quinidine
Q0010	Quinidine Sulfate Dihydrate
Q0028	Quinine
Q0030	Quinine Hydrochloride Dihydrate

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Oxazaborolidines

D2130

D2131

D2130	(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
D2131	(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine

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Chiral Phosphoric Acids

B1143

B1144

B1143	(R)-(-)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate
B1144	(S)-(+)-1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

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Chiral Diols

B2048	B1615	B1614
B1142	B1100

B2048	(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane
B1615	(+)-4,5-Bis[hydroxy(diphenyl)methyl]-2-methyl-2-phenyl-1,3-dioxolane
B1614	(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane
B1142	(R)-(+)-1,1'-Bi-2-naphthol
B1100	(S)-(-)-1,1'-Bi-2-naphthol

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Chiral Phase-Transfer Catalysts

D3475	D3476	B1683
B1689	B1684	B1685

D3475	6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Tetrafluoroborate [=(R,R)-TaDiAS-2nd]
D3476	6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2S,3S)-diylbis(methylammonium) Tetrafluoroborate [=(S,S)-TaDiAS-2nd]
B1683	N-Benzylcinchonidinium Chloride [Chiral Phase-Transfer Catalyst]
B1689	N-Benzylcinchoninium Chloride [Chiral Phase-Transfer Catalyst]
B1684	N-Benzylquinidinium Chloride [Chiral Phase-Transfer Catalyst]
B1685	N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst]

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Other Catalysts

B3296	B3549	D3808
D3809	T1215

B3296	(+)-Benzotetramisole
B3549	(-)-Benzotetramisole
D3808	(1R,2R)-N,N'-Dimethyl-N,N'-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine
D3809	(1S,2S)-N,N'-Dimethyl-N,N'-bis(3,3-dimethylbutyl)cyclohexane-1,2-diamine
T1215	Levamisole Hydrochloride

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Literature

1) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. Engl., 1971, 10, 496 [DOI]; Z. G. Hajos, D. R. Parrish, J. Org. Chem., 1974, 39, 1615 [DOI] .
2) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc., 2000, 122, 2395 [DOI].
3) Review: Acc. Chem. Res., 2004, 37(8), 487-631 [DOI], “ Asymmetric Organocatalysis” (special edition); H. Pellissier, Tetrahedron, 2007, 63, 9267 [DOI].
4) S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J., 2008, 14, 8079 [DOI].

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