Table 1.

Reductive chlorination of trityl hydrazones.

entry	hydrazone	chloride	yield[a]
1 11a			13a 82%
2 11b			13b 85%[b]
3 11c			13c 57% (3.4:1)
4 11d			13d 69% (2.9:1)
5 11e			13e 71% (1.3:1)
6 11f			13f 56%[b]
7 11g			13g 50%[c]
8 11h			13h 83% (21:1)
9 11i			13i 70% (2.6:1)
10 11j			13j 67%[d]

^[a]Isolated yields; diastereomeric ratio (dr) determined by ¹H NMR of purified chlorides and indicated in parentheses.

^[b]NMR yield.

^[c]Isolated yield for diastereomer shown (major), 2.8:1 crude dr.

^[d]Lithiated hydrazone treated with dichloramine-T.