Stereoselective Mannich Reactions in the Synthesis of Enantiopure Piperidine Alkaloids and Derivatives
نویسندگان
چکیده
Abstract: Piperidine alkaloids are members of the alkaloid family that is characterized by presence a six-membered nitrogen-containing heterocycle. found mainly in plants and often exhibit interesting biological pharmacological activities. Despite accumulation these natural products plants, relatively low quantities produced absolute terms thus synthesis derivatives thereof remains relevant to identify targets for drug discovery. Throughout years, researchers have come up with myriad methods synthesize piperidine derivatives. This review describes employ stereoselective Mannich reactions create core alkaloids. Asymmetric induction reaction has been achieved range divided into three conceptual approaches: (1) chiral pool-based (internal asymmetric induction), (2) auxiliary-based (relayed induction) (3) catalysis-based (external induction). Of each approach, we describe mechanism rationalize stereochemical outcome products.
منابع مشابه
Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline.
An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions...
متن کاملOne-pot synthesis of novel chiral β-amino acid derivatives by enantioselective Mannich reactions catalyzed by squaramide cinchona alkaloids.
An efficient one-pot synthesis of novel β-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral β-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a ch...
متن کاملStereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives
The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regioand stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electr...
متن کاملAsymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines.
Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99 : 1). The α-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the ...
متن کاملStereoselective Synthesis of Quinolizidine Alkaloids: (–)-Lasubin II
Initially, lasubin II was synthesized diastereoselectively in racemic form [3]. Asymmetric syntheses of lasubin II were achieved based on stereoselective transformations of enantiomerically pure substrates [4] or, for example, via a diastereoselective aza-Diels-Alder reaction using a resolved chiral arylaldehyde tricarbonylchromium complex [5]. Recently, an enantioselectively catalyzed aza-Diel...
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: European Journal of Organic Chemistry
سال: 2023
ISSN: ['1434-193X', '1099-0690']
DOI: https://doi.org/10.1002/ejoc.202300053