Zhang Xiaogang's Amnesia & Memory No. 10 (2004) is to lead Sotheby's Boundless sale of contemporary art in Hong Kong on January 20 with a $386,940-515,920 estimate.
The Amnesia & Memory series marked a shift in the artist's work, which had formerly explored Chinese history through a grand scope.
These later paintings focus on the individual, showing close ups of faces in monochrome.
Sotheby's explained: "The closed eyes deny the viewer any direct psychological engagement with the subject.
"Instead, the cropping of the figure and the focus on the eyes draw the figure into a dream-like space, exempt from the conformity that had previously been imposed on so many of Zhang's subjects. "
A Robert Indiana LOVE sculpture, one of an edition of eight, is another highlight, with a valuation of $283,756-412,736.
Indiana produced the iconic design for a Museum of Modern Art Christmas card in 1964. It later became a symbol of the hippy movement.
Indiana began to make the sculptures in 1966, many of which were installed in public spaces around the US - most notably in Philadelphia's John F Kennedy Plaza (which came to be known as Love Park).
The present lot was executed in 2000. Another example sold for $1.6m last year.
Please sign up to our free newsletter to receive exciting news about art and antiques auctions.