Abstract
Abstract The cyclization of (+)-cis-1,2,2-trimethyl-1,3-diaminocyclopentane 1 with thiophosphorodichloridates 2 or O-(4-nitrophenyl)thiophosphorochloridates 4 forms (+)-2,4,5-diazaphosphabicyclo[3.2.1]octane 3 and 3′, respectively, but the stereoselectivity arising from the condensation of (+)-1 with 4 is less than that of (+)-1 with 2. The distinction between the two product distributions might be due to the significance of different mechanistic routes. In the light of a trigonal bipyramid (TBP) intermediate and Berry pseudorotation (BPR) concept their mechanism are discussed.
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