Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet-Spengler theme.
نویسندگان
چکیده
An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile.
منابع مشابه
Thiourea-catalyzed enantioselective iso-Pictet-Spengler reactions.
A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-protected products by trituration or crystallization provides the optically pure tetrahydro-γ-carboline derivatives in a scalable and highly pract...
متن کاملWeak Brønsted acid-thiourea co-catalysis: enantioselective, catalytic protio-Pictet-Spengler reactions.
The development of one-pot imine formation and asymmetric Pictet-Spengler reactions cocatalyzed by a chiral thiourea and benzoic acid is described. Optically active tetrahydro-beta-carbolines, ubiquitous structural motifs in biologically active natural products, are obtained in high ee directly from tryptamine and aldehyde precursors.
متن کاملSolid-phase synthesis of 1,2,3, 4-tetrahydro-beta-carboline-containing peptidomimetics.
A solid-phase method for the synthesis of 1,2,3, 4-tetrahydro-beta-carboline-containing peptidomimetics has been developed. The key step in the strategy is the Pictet-Spengler condensation of a resin-bound tryptophan-containing fragment with an Fmoc-amino aldehyde.
متن کاملTraceless synthesis of hydantoin fused tetrahydro-beta-carboline on ionic liquid support in green media.
A novel ionic liquid (IL) supported, green synthetic protocol has been developed toward the synthesis of oxo and thio hydantoin analogues tethered with tetrahydro-beta-carboline by the use of focused microwave irradiation. IL-bound tryptophan underwent a Pictet-Spengler reaction with various carbonyl compounds to generate the IL-immobilized tetrahydro-beta-carbolines in aqueous isopropanol medi...
متن کاملCatalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-β-carbolines by phase-transfer catalyzed alkylations.
Efficient catalytic asymmetric synthesis of 1,1-disubstituted tetrahydro-β-carbolines has been achieved via asymmetric alkylation of 1-cyanotetrahydro-β-carbolines using a binaphthyl-modified N-spiro-type chiral phase-transfer catalyst. This is a valuable example of hitherto difficult highly enantioselective alkylations at α-carbon of the cyano group under phase-transfer conditions.
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:
- Chemical communications
دوره 48 27 شماره
صفحات -
تاریخ انتشار 2012