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Diastereoselective Spirocyclization via Intramolecular C( sp 3 )−H Bond Functionalization Triggered by Sequential [1,5]‐Hydride Shift/Cyclization Process: Approach to Spiro‐tetrahydroquinolines
Author(s) -
Bhowmik Arup,
Das Sumit,
Sarkar Writhabrata,
Saidalavi K. M.,
Mishra Aniket,
Roy Anupama,
Deb Indubhusan
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001011
Subject(s) - chemistry , hydride , lewis acids and bases , intramolecular force , catalysis , surface modification , lewis acid catalysis , combinatorial chemistry , medicinal chemistry , methylene , stereochemistry , organic chemistry , hydrogen
A direct synthesis of spiro[5.5]and [5.4]‐tetrahydroquinolines has been developed through C( sp 3 )−H bond functionalization triggered by sequential [1,5]‐ hydride shift /cyclization sequence using ortho amino benzaldehydes and active methylene compounds such as 2‐coumaranone, 4‐hydroxycoumarin, 3‐coumaranone, and 3‐isochromanone. This protocol provides a Lewis acid catalyst‐free straight forward one‐pot reaction in cases of 2‐coumaranone and 4‐hydroxycoumarin, Lewis acid‐catalyzed stepwise reaction for 3‐coumaranone and 3‐isochromanone to access a wide range of spiro‐heterocycles in excellent to good yields and diastereoselectivity.