Diastereoselective Spirocyclization via Intramolecular C( sp  3 )−H Bond Functionalization Triggered by Sequential [1,5]‐Hydride Shift/Cyclization Process: Approach to Spiro‐tetrahydroquinolines | Zendy

Bhowmik Arup | Zendy; Das Sumit | Zendy; Sarkar Writhabrata | Zendy; Saidalavi K. M. | Zendy; Mishra Aniket | Zendy; Roy Anupama | Zendy; Deb Indubhusan | Zendy

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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.

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