Computer-assisted discovery of novel amino acid derived sulfides for enantioselective epoxidation of aldehydes

Myllymäki, Vesa T; Lindvall, Mika K.; Koskinen, Ari M. P.

doi:10.1016/s0040-4020(01)00396-9

Cited by 40 publications

(15 citation statements)

References 24 publications

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“…137 Aggarwal thus conducted a computational study of the transition states of this methodology, involving realistic model molecules with solvation effects. 138 They studied the reaction of a phenyl stabilized ylide (PhCH=SMe 2 ) with benzaldehyde at the B3LYP/6-311+G(d, p)//B3LYP/6-31G(d) level.…”

Section: Lewis/brønsted Base Catalysismentioning

confidence: 99%

Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities

et al. 2011

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Section: Lewis/brønsted Base Catalysismentioning

confidence: 99%

Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities

et al. 2011

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“…The methodology involved the conversion of Boc-valinol into the corresponding thioacetate using thioacetic acid under Mitsunobu conditions, followed by KOH-mediated hydrolysis. 18 Yang's group described the synthesis of 1,2-substituted amino thiols using dibenzyl-protected 1,2-substituted b-amino thioacetates. 19 An alternative route for the synthesis of amino thiols employing methyl dithioacetate as a sulfur transfer reagent is also known.…”

Section: Methodsmentioning

confidence: 99%

A Simple Synthesis of Nβ-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of Nβ-Fmoc/Z-Amino Alkyl Sulfonic Acids

Sureshbabu¹,

Vishwanatha²,

Vasantha³

2010

Synlett

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A simple and efficient protocol for the synthesis of N bFmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides.

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“…Another type of sulfide catalyst, thiazolidine derivatives of type 220, were designed by the Koskinen group with the aid of molecular modeling [221]. In the model reaction the thiazolidine 220 catalyzed the formation of the trans epoxide (S,S)-trans-202a highly enantioselectively (90% ee) although the yield (16%) was low (Scheme 6.98).…”

Section: Epoxide Formation From Ylides Prepared By Metal-catalyzed Camentioning

confidence: 99%

Nucleophilic Addition to CO Double Bonds

Berkessel

Gröger

2005

Asymmetric Organocatalysis

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H CN HO 97 %, 97 % ee (ref. 23) 83 %, >98 % ee (ref. 26) H CN HO 61 %, 91 % ee (ref. 23) H CN HO 76 %, 93 % ee (ref. 23) H 3 CO H CN HO 78 %, 96 % ee (ref. 23) H 3 C H CN HO H 3 C 95 %, 91 % ee (ref. 22) H CN HO H 3 CO 83 %, 97 % ee (ref. 23) H CN HO PhO 97 %, 92 % ee (ref. 23) 84 %, 95 % ee (ref. 26) H CN HO 85 %, 83 % ee (ref. 22) H 3 CO H CN HO 45 %, 84 % ee (ref. 23) OCH 3 H CN HO 90 %, 80 % ee (ref. 22) F 3 C H CN HO 50 %, 89 % ee (ref. 22) N H H 3 C O O H O 76 %, 93 % ee (ref. 22) Scheme 6.2 132 6 Nucleophilic Addition to CbO Double Bonds 1: 83 %, 97 % ee (R ) (ref. 23) 2: 89 %, 56 % ee (S ) (ref. 33) t-Bu H O 91 %, 66 % ee (ref. 33) i-Pr H O 83 %, 64 % ee (ref. 33) H O 98 %, 74 % ee (ref. 33) n-C 5 H 11 H O 93 %, 81 % ee (ref. 33)

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Computer-assisted discovery of novel amino acid derived sulfides for enantioselective epoxidation of aldehydes

Cited by 40 publications

References 24 publications

Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities

Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities

A Simple Synthesis of Nβ-Fmoc/Z-Amino Alkyl Thiols and their use in the Synthesis of Nβ-Fmoc/Z-Amino Alkyl Sulfonic Acids

Nucleophilic Addition to CO Double Bonds

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