Enzymatic and Chemoenzymatic Three‐Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines
نویسندگان
چکیده
Chemoenzymatic and enzymatic cascade reactions enable the synthesis of complex stereocomplementary 1,3,4-trisubstituted tetrahydroisoquinolines (THIQs) with three chiral centers in a step-efficient and selective manner without intermediate purification. The cascade employs inexpensive substrates (3-hydroxybenzaldehyde and pyruvate), and involves a carboligation step, a subsequent transamination, and finally a Pictet-Spengler reaction with a carbonyl cosubstrate. Appropriate selection of the carboligase and transaminase enzymes enabled the biocatalytic formation of (1R,2S)-metaraminol. Subsequent cyclization catalyzed either enzymatically by a norcoclaurine synthase or chemically by phosphate resulted in opposite stereoselectivities in the products at the C1 position, thus providing access to both orientations of the THIQ C1 substituent. This highlights the importance of selecting from both chemo- and biocatalysts for optimal results.
منابع مشابه
One-pot synthesis of 2,4,5-trisubstituted imidazoles catalyzed by dicationic magnetic room temperature ionic liquid
Regarding the green chemistry's goals, dicationic magnetic room temperature ionic liquid open up new avenue to introduce an amazing and efficient system for facilitating catalyst recovery in different organic reactions. Ability of this dicationic magnetic room temperature ionic liquid catalyst in the one-pot three-components condensation reaction of benzil, aromatic aldehyde, and ammonium aceta...
متن کاملOne-pot synthesis of 2,4,5-trisubstituted imidazoles catalyzed by dicationic magnetic room temperature ionic liquid
Regarding the green chemistry's goals, dicationic magnetic room temperature ionic liquid open up new avenue to introduce an amazing and efficient system for facilitating catalyst recovery in different organic reactions. Ability of this dicationic magnetic room temperature ionic liquid catalyst in the one-pot three-components condensation reaction of benzil, aromatic aldehyde, and ammonium aceta...
متن کاملNatural Biopolymers is an Efficient Catalyst for the Synthesis of 1,3,5-Trisubstituted Pyrazoles
Cellulose sulfuric acid is an efficient metal-free catalyst for the synthesis of 1,3,5-trisubstituted pyrazoles via the condensation of 1,3-diketones and hydrazines. The reaction was carried out in Solvent-free condition at room temperature and the products were isolated in good to excellent yields. Mild reaction conditions, as well as ease of operation and workup are some advantages of the pro...
متن کاملNano-SbCl5/SiO2 as an Efficient Catalyst for One-Pot Synthesis of 2, 4, 5-Trisubstituted Imidazoles Under Solvent- Free Condition
A general synthetic route to the synthesis of imidazoles has been developed using nano SbCl5/SiO2 under solvent-free conditions. The multi-component reactions of aldehydes, benzil and ammonium acetate were carried out to afford some trisubstituted imidazole derivatives. This method provides several advantages like simple work-up, environmentally benign, and shorter reaction times along wi...
متن کاملCaro’sacid-silicagel: An Efficient and Reusable Catalyst for the Synthesis of 2, 4, 5- Trisubstituted Imidazoles under Solvent-free Conditions
Caro’s acid-silicagel was found to be a mild and effective catalyst for the one –pot multicomponent condensation of benzyl, aldehydes and ammonium acetate used for synthesis of 2, 4, 5-trisubstituted imidazole derivatives under solvent–free conditions. This catalyst has several advantages such as simple work-up, low cost and reusability.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 56 شماره
صفحات -
تاریخ انتشار 2017