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Stereodivergent Dual Catalytic α‐Allylation of Protected α‐Amino‐ and α‐Hydroxyacetaldehydes
Author(s) -
Sandmeier Tobias,
Krautwald Simon,
Zipfel Hannes F.,
Carreira Erick M.
Publication year - 2015
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.201506933
Subject(s) - allylic rearrangement , aldehyde , amine gas treating , catalysis , chemistry , combinatorial chemistry , selectivity , organic chemistry
Fully stereodivergent dual‐catalytic α‐allylation of protected α‐amino‐ and α‐hydroxyacetaldehydes is achieved through iridium‐ and amine‐catalyzed substitution of racemic allylic alcohols with chiral enamines generated in situ. The operationally simple method furnishes useful aldehyde building blocks in good yields, more than 99 % ee , and with d.r. values greater than 20:1 in some cases. Additionally, the γ,δ‐unsaturated products can be further functionalized in a stereodivergent fashion with high selectivity and with preservation of stereochemical integrity at the C α position.