Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi-Contiguous Stereocenters via Sequential Catalysis.

Area of Science:

• Organic Chemistry
• Asymmetric Catalysis
• Synthetic Methodology

Background:

• Aliphatic nitro compounds are versatile synthetic intermediates.
• Efficient construction of multiple stereocenters remains a challenge in organic synthesis.

Purpose of the Study:

• To develop a highly efficient and stereoselective synthesis of aliphatic nitro compounds with multi-contiguous stereocenters.
• To achieve stereodivergent synthesis of nonadjacent stereocenters.

Main Methods:

• Copper-catalyzed asymmetric conjugate addition of dialkylzinc reagents to nitroalkenes.
• Iridium-catalyzed asymmetric allylic substitution reaction.
• Sequential application of two chiral catalysts with different enantiomers.

Main Results:

• High yields (up to 72%) of nitro compounds with multiple stereocenters.
• Excellent diastereoselectivity (up to 12:1 dr) and enantioselectivity (up to >99% ee).
• Stereodivergent control of 1,3-nonadjacent stereocenters was achieved.

Conclusions:

• The combined catalytic system provides a powerful strategy for constructing complex chiral nitroalkanes.
• This method enables precise control over stereochemistry, facilitating access to valuable chiral building blocks.