Asymmetric fluorination of α-branched aldehydes catalyzed by chiral primary amines under mild conditions has been developed. Both enantiomers could be obtained with good yields (up to 96%) and a high enantioselectivity (up to 90% ee) by a simple swap of the fluorination reagents.
N,O-acetals (NOAcs) were developed as bench stable surrogates for N-carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β-ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α- or β-amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner.
A simple chiral primary amine catalyst was identified to enable effective catalysis in direct α-sulfenylation of acyclic and cyclic β-ketocarbonyls with good yields and excellent enantioselectivities.
N,O‐acetals (NOAcs) were developed as bench stable surrogates for N‐carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β‐ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α‐ or β‐amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner.
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