Metal‐Catalyzed Regiodivergent Cyclization of γ‐Allenols: Tetrahydrofurans versus Oxepanes | Zendy

Alcaide Benito | Zendy; Almendros Pedro | Zendy; Martínez del Campo Teresa | Zendy

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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).

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