Stereospecific construction of a trans-1,4-diphosphacyclohexane skeleton

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1489-1492

  Morisaki, Yasuhiro ^a   Imoto, Hiroaki ^a   Ouchi, Yuko ^a   Nagata, Yuuya ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 59849090940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800261j     Document Type: Article

References (45)

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38. The reaction without amine or with other amines such as N,N,N′,N′-tetramethylethylenediamine (TMEDA) as a ligand proceede smoothly to obtain the corresponding 1,4-diphosphacyclohexane; however, the best result was obtained when (-)-sparteine was employed in the lithiation step.
39. The oxidative intramolecular coupling reaction of enantiomer (R,R)-1 also provides the trans isomer (trans-2) stereospecifically. Synthesis of (R,R)-1a was reported by Imamoto and Crépy: Imamoto, T.; Crépy K. V. L. Tetrahedron Lett. 2002, 43, 7735.
40. w = 0.137, GOF = 1.092.
41. ORTEP drawing of trans-2a is shown in Figure S14 in the Supporting Information, although a desired single crystal could not be obtained.
42. The stereoselective or stereospecific synthesis of meso-1 has not yet been achieved and challenged.
43. Original spectra are shown in Figures S9 and S10 in the Supporting Information.
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