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Abstract
The enzyme-catalyzed monoacetylation of prochiral bis (2-hydroxymethylphenyl)methylphosphine and bis (2-hydroxymethylphenyl)phenylphosphine and their P-sulfides gave, in one single step, as a result of desymmetrisation, the corresponding monoacetates in moderate yields and with an enantiomeric excess of 16 to 98%, depending on the substrate structure and enzyme applied. The absolute configurations of the selected products were determined by a chemical correlation. This led to the conclusion that, in the case of phosphines, phosphine oxides and phosphine sulfides enzymes preferentially produce compounds of the same spatial arrangement. The new compounds obtained will be transformed into chiral catalysts/ligands.
Highlights
Since the pioneering times of the mid-1970s, when the first practical and generally applicable methods in asymmetric synthesis [1] were developed, there has been a tremendous growth in this research field
We decided to synthesize catalysts in which the stereogenic sulfinyl moiety was replaced by a stereogenic phosphorus-containing group
We synthesized the enantiomerically pure (2-acetoxymethylphenyl)(2’-hydroxymethylphenyl)phosphine oxide 5, which was planned to be a precursor of the desired ligSaSncchdhesemm6ee(1S1.c.ShSyeynmntthheees2si)is.sooffcchhiirraallttrriiddeennttaatteessuullffiinnyyllccaattaallyyssttss
Summary
Since the pioneering times of the mid-1970s, when the first practical and generally applicable methods in asymmetric synthesis [1] were developed, there has been a tremendous growth in this research field. Searching for new chiral catalysts, we synthesized some time ago a series of organosulfur chiral compounds 3, containing a stereogenic sulfinyl moiety, an enantiomeric amine fragment and the hydroxyl group (Scheme 1) [10,11] They proved to be excellent catalysts in a variety of reactions of asymmetric synthesis [9,12]. We synthesized the enantiomerically pure (2-acetoxymethylphenyl)(2’-hydroxymethylphenyl)phosphine oxide 5, which was planned to be a precursor of the desired ligSaSncchdhesemm6ee(1S1.c.ShSyeynmntthheees2si)is.sooffcchhiirraallttrriiddeennttaatteessuullffiinnyyllccaattaallyyssttss Following these positive results, we decided to synthesize catalysts in which the stereogenic sulfinyl moiety was replaced by a stereogenic phosphorus-containing group. FAtefrtecromcopmleptiloetni,otnh,ethenezeynmzyesmweserwe efirletfielrteedredofof,fft,htehesoslovlevnetnat nadndexecxecsesssoof fvvininyyl laacceetatatetewweerreeeevvaappoorraatteedd,,aanndd tthhee rreessiidduuee wwaass separated via column chromatography In this case, the formation of achiral diacetates 26 and 27 was observed, which, in some cases, may be responsible for a decreased yield of monoacetates.
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