Diastereoselective dielsalder reactions chiral dienes diastereoselection 82 from chemistry 206 at university of texas, rio grande valley. Iminium ions derived from s5phenylmorpholin2one 1 undergo diastereoselective strecker reactions using copperi cyanide and anhydrous hydrochloric. General mechanism of the strecker amino acid synthesis. Primary and secondary amines derived from l amino acids were used as sources of chirality. An example of modest stereoselectivity is the dehydrohalogenation of 2iodobutane which yields 60% trans2butene and 20% cis2butene. A novel route to 2s,3s and 2r,3s2amino3,4dihydroxybutyric acid efficient and. Ironiii chloride as a watercompatible lewis acid for. Diastereocontrolled strecker reaction using s5phenylmorpholin. Sager, journalangewandte chemie, year1987, volume26, pages557559. Diastereoselective strecker reaction of dglyceraldehyde. The diastereoselectivity was found to be highly dependent on the substituent of the oxazolidinone moiety.
Jun 06, 2003 highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines binfeng li,a ke yuan,a mingjie zhang,a hao wu,b lixin dai,a quan rui wangb and xuelong houa. Binfeng li, ke yuan, mingjie zhang, hao wu, linxin dai, quan rui wang, xuelong hou. Pdf diastereoselective and enantioselective mukaiyama. This protocol allows direct use of nfree isatin substrates.
Jul 18, 2003 multicomponentstrecker reaction under high pressure. The strecker reaction is accompanied by an in situ. Apr 11, 2012 a diastereoselective strecker reaction using r. Pdf diastereoselective and enantioselective mukaiyama aldol. Diamino acid derivatives were also obtained in high diastereoselectivity from the reaction of 2aziridinesulfinimines 1h and 1i followed by ringopening of the products with thiophenol. Aug 23, 2004 the strecker reaction has gained considerable attention due to its significance in the synthesis of.
Highly diastereoselective strecker reaction of enolizable. The strecker reaction has gained considerable attention due to its significance in the synthesis of. Jul 21, 2014 a practical and efficient method for preparation of highly enantiomerically enriched 3cyano3aminooxindoles and 3trifluoromethyl3aminooxindoles with up to 99% optical purity by a lewis acid promoted diastereoselective strecker reaction and trifluoromethylation of isatinderived ntertbutanesulfinyl ketimines has been developed. A diastereoselective strecker reaction leading to enantiopure. Catalytic asymmetric strecker reaction still a new and hot area. In this screencast, andrew parsons defines diastereomers and walks you through examples of diastereoselective reactions. Diastereoselective strecker reaction of imines derived. Diastereoselective strecker reaction of imines derived from d.
Diastereoselective and enantioselective mukaiyama aldol reactions of. Highly stereoselective strecker reaction of chiral. How to do synthesis nucleophiles and electrophiles. Asymmetric catalysis of the strecker amino acid synthesis by a cyclic. Strecker reactions of chiral nacylhydrazones semantic scholar. The synthesis of a series of new chiral alphaaminonitriles was achieved in a diastereoselective strecker reaction in a onepot procedure with aldehydes, enantiopure. Chakraborty tk, reddy gv, hussain ka 1991 diastereoselective strecker. Primary and secondary amines derived from lalphaamino acids were used as sources of chirality. Stereoselective synthesis of a dialkylhydantoin featuring an. Strecker synthesis an overview sciencedirect topics.
Diastereoselective strecker synthesis of aminonitriles on. Therefore, we presumed that our chiral anion generator can be applied to catalytic enantioselective strecker synthesis by generating a chiral. Multicomponentstrecker reaction under high pressure. Stereoselective synthesis of a dialkylhydantoin featuring. Diastereoselective dielsalder reactions chiral dienes. Scalable organocatalytic asymmetric strecker reactions catalysed by.
The stereocontrolled synthesis of hydroxyctamino acids, which can be found in a number of biologically active compounds 1 such as peptides, peptidases. Jun 15, 2012 it allowed the synthesis of natural 3,4,5. Double reductive amination and selective strecker reaction. A diastereoselective strecker type reaction of imines derived from conveniently protected d glyceraldehyde has been achieved with good to excellent stereoselectivity through an appropriate choice of the protecting group and reaction conditions the stereocontrolled synthesis of hydroxyctamino acids, which can be found in a. This work is licensed under a creative commons attributionnoncommercial 3. Wang and xuelong hou, journalthe journal of organic chemistry, year2003. Asymmetric synthesis of 3,5bisisopropyloxy4methoxyphenyl.
Jul 08, 1996 diastereoselective strecker reaction of dglyceraldehyde derivatives. Development of a method for addition of trimethylsilyl cyanide to chiral oxazolidinonederived nacylhydrazones is described. Amino acids via a crystallizationinduced asymmetric transformation using r phenylglycine amide as chiral auxiliary organic letters, 2001 jeanpaul seerden. Asymmetric strecker synthesis of arylglycines request pdf. Since alkene geometric isomers are also classified as diastereomers, this reaction would also be called diastereoselective the addition of formic acid to norbornene is also stereospecific because the exo isomer is formed exclusively without any of. Asymmetric strecker reaction using chiral amine auxiliary harada, k. For more information, read michigan publishings access and usage policy. Two short syntheses of dnboc3,5bisisopropyloxy4methoxyphenylglycine, a central unit of vancomycin type antibiotics, have been developed.
A novel route to 2 s,3 s and 2 r,3 s 2amino3,4dihydroxybutyric acid author links open overlay panel carlos cativiela. The method is used commercially for the production of racemic. The reaction gives modest selectivity with aliphatic hydrazones. The strecker reaction is one of the most attractive methods for the synthesis of.
Since alkene geometric isomers are also classified as diastereomers, this reaction would also be called diastereoselective. The diastereoselective strecker reaction of enolizable aliphatic sulfimines proved to be significantly more efficient 23, 24 and is outlined in scheme 2. Diastereoselective strecker reaction of 4,4,4trifluorobutanal 17 with r. An efficient and practical procedure for strecker reaction. Diastereoselective strecker synthesis of aminonitriles on carbohydrate templates related. Lewis acid promoted diastereoselective addition of tmscn. Diastereoselective aldol reactions of various aldehydes with silicon enolates in water have been successfully carried out using ironiii chloride and a surfactant. Jan 09, 2003 read highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines.
Stereochemistry diastereoselective and enantioselective reactions. Lewis basecatalyzed diastereoselective streckertype. Aldehydes were coupled with enantiopure amines derived from l. Diastereoselective strecker reactions based on rphenylglycine amide as chiral auxiliary are reported. Aug 24, 2020 a stereoselective reaction in which the possible products are diastereomers is said to be diastereoselective.
The synthesis of a series of new chiral aminonitriles was achieved in a diastereoselective strecker reaction in a one. A series of new chiral aminonitriles was obtained in a diastereoselective strecker reaction. Double reductive amination and selective strecker reaction of. The strecker amino acid synthesis, also known simply as the strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonium chloride in the presence of potassium cyanide. Apr 8, 2015 ericminikel cambridge, ma chem20 these are my notes from lecture 25 of harvards chemistry 20.
The synthesis of a series of new chiral alphaaminonitriles was achieved in a diastereoselective strecker reaction in a onepot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Diastereoselective strecker reaction of dglyceraldehyde derivatives. A diastereoselective strecker amination reaction using sphenylglycinol as a chiral inducer was the key step in the first synthesis, while evans electrophilic azidation technol. Contrary to previous understanding, ironiii chloride has been shown to be a watercompatible lewis acid. Abstract for abstract see cheminform abstract in full text. The reaction gives modest selectivity with aliphatic. Highly diastereoselective strecker reaction of enolizable aliphatic sulfinimines. Synthesis of 7methoxybenzolactamv8 using a diastereoselective strecker synthesis. Amino acids via a crystallizationinduced asymmetric transformation using r phenylglycine amide as chiral auxiliary. Since 2 and 3 are diastereomers, the overall reaction between 1 and h 2 is diastereoselective.
1237 10 1111 1052 640 1266 1286 562 1519 621 206 91 133 10 893 1607 1387 1473 669 44 120 648 596 1678 1338 1572 1667 1700 815 1327 147 91 443