Catalyst-Controlled Multicomponent Aziridination of Chiral Aldehydes.
نویسندگان
چکیده
A highly diastereoselective and enantioselective method for the multicomponent aziridination of chiral aldehydes has been developed with BOROX catalysts of the VANOL (3,3'-diphenyl-2,2'-bi-1-naphthol) and VAPOL (2,2'-diphenyl-(4-biphenanthrol)) ligands. Very high to perfect catalyst control is observed with most all substrates examined including aldehydes with chiral centers in the α- and β-positions. High catalyst control was also observed for a number of chiral heterocyclic aldehydes allowing for the preparation of epoxy aziridines, bis(aziridines) and ethylene diaziridines. Application of this reaction in the synthesis of β3 -homo-d-alloisoleucine and β3 -homo-l-isoleucine is reported.
منابع مشابه
Multicomponent catalytic asymmetric aziridination of aldehydes.
The first multicomponent catalytic asymmetric aziridination reaction is developed to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity from aromatic and aliphatic aldehydes. This new method pushes the boundary of the aziridination reaction to substrates that failed with preformed imines.
متن کاملControlled diastereo- and enantioselection in a catalytic asymmetric aziridination.
Chiral polyborate based Brønsted acids prepared from the VANOL and VAPOL ligands are known to catalyze the reaction of diarylmethyl imines with diazoesters to give cis-aziridines. In the present work, this same catalyst is shown to catalyze the reaction of the same imines with diazoacetamides to give trans-aziridines with the same high asymmetric inductions as seen with cis-aziridines, enabling...
متن کاملMapping the active site in a chemzyme: diversity in the N-substituent in the catalytic asymmetric aziridination of imines.
The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imi...
متن کاملTotal synthesis of sedum alkaloids via catalyst controlled aza-Cope rearrangement and hydroformylation with formaldehyde.
The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formalde...
متن کاملLayered Double Hydroxides (LDHs): An Efficient Catalyst System for the Synthesis of Chiral Aminonitriles
Strecker reaction is one of the simplest multicomponent reactions. It used for synthesis of chiral α-amino nitriles. This reaction was carried out in the presence of catalytic amount of layered double hydroxides (LDHs). In this study, simple and practical method for the synthesis of this class of catalysts is provided. The results shown that LDH is the good heterogen catalyst for synthesis of c...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemistry
دوره 23 11 شماره
صفحات -
تاریخ انتشار 2017