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Metal‐Catalyzed Regiodivergent Cyclization of γ‐Allenols: Tetrahydrofurans versus Oxepanes
Author(s) -
Alcaide Benito,
Almendros Pedro,
Martínez del Campo Teresa
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701611
Subject(s) - ringing , metal , scheme (mathematics) , database , chemistry , computer science , stereochemistry , mathematics , telecommunications , organic chemistry , enhanced data rates for gsm evolution , mathematical analysis
Ringing the changes : The 5‐ exo‐trig cyclization pathway of γ‐allenols can be completely reversed by either changing the metal (Pd instead of Au) or using a (methoxymethyl)oxy protecting group. As a result, the 7‐ endo‐trig alkoxycyclization dominates instead (see scheme; MOM=MeOCH 2 ; Z 1 = t BuMe 2 Si, ArCO).