Tripeptide Organocatalysts for Stereoselective Conjugate Addition Reactions with N‐Heterocyclic Substituents
نویسندگان
چکیده
N-heterocyclic moieties are abundant among pharmaceuticals and agrochemicals, but a challenge for metalorganic organocatalytic transformations. We present tripeptides of the type H-Pro-Pro-Xaa as catalysts stereoselective conjugate addition reactions between substituted aldehydes electrophiles. Alkyl substituents at N-terminal proline, reactive site, were crucial high chemo- stereoselectivity. Different moieties, even both reaction partners, readily tolerated products obtained in yields 61–95% enantioselectivities up to 98% ee.
منابع مشابه
Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones.
The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-beta-amino ester enolates, generated by lithium amide conjugate addition to an alpha,beta-unsaturated ester or deprotonation of a beta-amino ester, respectively, to a range of alpha,beta-unsaturated acceptors has been investigated. Deprotonation of a beta-amino ester with LDA, followed by conjugate addition to...
متن کاملConjugate addition–enantioselective protonation reactions
The addition of nucleophiles to electron-deficient alkenes represents one of the more general and commonly used strategies for the convergent assembly of more complex structures from simple precursors. In this review the addition of diverse protic and organometallic nucleophiles to electron-deficient alkenes followed by enantioselective protonation is summarized. Reactions are first categorized...
متن کاملPeptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes and Ketones to Maleimides
This thesis describes the development of peptidic catalysts for stereoselective conjugate addition reactions of aldehydes and ketones to maleimides. In addition, mechanistic aspects of this conjugate addition were investigated and structural aspects of peptidic catalysts of the general H-DPro-Pro-type were studied. From a collection of tripeptides, H-DPro-Pro-Asn-NH2 was found to catalyze the c...
متن کاملCu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates.
The CuOAc-catalyzed reaction of internal alkynoates with arylboronic acids proceeded under mild conditions to yield trisubstituted cinnamates stereoselectively.
متن کاملCopper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addi...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Advanced Synthesis & Catalysis
سال: 2022
ISSN: ['1615-4169', '1615-4150']
DOI: https://doi.org/10.1002/adsc.202200576