First synthesis of P-chirogenic prophosphatranes

作者：Zhou Yibo; Armstrong Daniel W; Zhang Ying; Verkade John G^*

来源：Tetrahedron Letters, 2011, 52(14): 1545-1548.

DOI：10.1016/j.tetlet.2011.01.041

• Prophosphatrane
• P-Chirogenic
• Resolution
• Enantiomeric
• Catalyze

Syntheses are reported for the novel P-chirogenic bicyclic prophosphatranes P(RNCH(2)CH(2))(2)N(OCH(2)CH(2))-(8) in which the two R groups [i.e., 1-methylenenaphthyl and 1,2-methoxybenzyl (8)] and in its corresponding phosphine oxide (9) are different. Also synthesized was the transannulated protonated phosphatrane cation in the salt [HP(RNCH(2)CH(2))(3)N]Cl in which the three R groups [i.e., 1-methylenenaphthyl, 1,2-methoxybenzyl, and (S)-1-phenethyl (14)] are different, and also in its corresponding deprotonated prophosphatrane form P(RNCH(2)CH(2))(3)N (15). Good analytical resolution of racemic 9 is reported, whereas only partial resolution was achieved for diastereomeric 14.

• 出版日期2011-4-6