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Catalytic Sc( OTf ) 3 mediated direct asymmetric aldol reaction of (−)‐menthyl isothiocyanatoacetate with aldehydes by using (−)‐menthol as chiral auxiliary
Author(s) -
Bhangare Dattatraya N.,
Shinde Rohit G.,
Pawar Pushpalata D.,
Nikalje Milind D.,
Lokhande Mahendra N.
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4286
Subject(s) - chemistry , aldol reaction , menthol , catalysis , oxazolidine , organic chemistry , aldehyde , enantioselective synthesis , reaction conditions , combinatorial chemistry , medicinal chemistry
This method involves the direct asymmetric aldol reaction of (−)‐menthyl isothiocyanatoacetate 5 with a variety of substituted aromatic aldehydes, which offers a convenient method for the synthesis of intermediate containing biologically relevant α‐amino β‐hydroxyl groups in oxazolidine ring. In this methodology, the products show remarkable diastereoselectivity using Sc(OTf) 3 as a catalyst and easily accessible (−)‐menthol as a chiral auxiliary. This approach includes some important aspects such as mild reaction conditions, high yields, and excellent diastereoselectivity with a number of substituted aromatic aldehydes. The optimization and effect of different catalysts were studied at different reaction conditions and it is found that Sc(OTf) 3 shows excellent diastereoselectivity at −45°C.