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New Strategies for the Efficient Synthesis of Medium‐Sized Bicyclic γ‐Alkylidenebutenolides Based on Regioselective Cyclizations of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with Oxalyl Chloride
Author(s) -
Langer Peter,
Eckardt Tobias,
Saleh Nehad N. R.,
Karimé Inass,
Müller Peter
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200110)2001:19<3657::aid-ejoc3657>3.0.co;2-5
Subject(s) - bicyclic molecule , chemistry , oxalyl chloride , regioselectivity , enol , metathesis , ring closing metathesis , cycloaddition , chloride , organic chemistry , combinatorial chemistry , catalysis , polymerization , polymer
Medium‐sized bicyclic γ‐alkylidenebutenolides were efficiently prepared by Me 3 SiOTf‐catalyzed cyclization of cyclic bis(silyl enol ethers) with oxalyl chloride. In addition, a new strategy for the synthesis of medium‐sized bicyclic hybrids of butenolides and medium‐sized cyclic ethers − based on sequential [3+2] cyclization of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes, Mitsunobu reaction, and ring‐closing metathesis − is reported.