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Volumn 11, Issue 19, 2009, Pages 4470-4473

Steric tuning of the amidomonophosphane-rhodium(l) catalyst in asymmetric addition of arylboroxines to n-phosphinoyl aldimines

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; IMINE; METHYLAMINE; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE; RHODIUM;

EID: 70350192265     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901866y     Document Type: Article
Times cited : (34)

References (50)
  • 10
    • 0025144699 scopus 로고
    • Selected examples for asymmetric synthesis of diarylmethylamines
    • Selected examples for asymmetric synthesis of diarylmethylamines: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681-6684.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6681-6684
    • Tomioka, K.1    Inoue, I.2    Shindo, M.3    Koga, K.4
  • 19
    • 0025728076 scopus 로고
    • Selected examples of catalytic asymmetric alkylation of imines
    • Selected examples of catalytic asymmetric alkylation of imines: (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1991, 32, 3095-3098.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3095-3098
    • Tomioka, K.1    Inoue, I.2    Shindo, M.3    Koga, K.4
  • 42
    • 70350200549 scopus 로고    scopus 로고
    • The first "a" and second "a" of 6aa are derived from the suffixes of 3a and 4a, respectively.
    • The first "a" and second "a" of 6aa are derived from the suffixes of 3a and 4a, respectively.
  • 44
    • 70350190859 scopus 로고    scopus 로고
    • The Ar-Rh(I) species is formed by transmetalation between rhodium(I) and arylboroxine at the trans side to phosphorus, which is the most vacant coordination site and influenced by the trans effect of phosphine. See ref 17.
    • The Ar-Rh(I) species is formed by transmetalation between rhodium(I) and arylboroxine at the trans side to phosphorus, which is the most vacant coordination site and influenced by the trans effect of phosphine. See ref 17.
  • 46
    • 70350204893 scopus 로고
    • 2 and 3,5-diphenylphenylmagnesium bromide, which was prepared from, known aryl bromide.
    • 2 and 3,5-diphenylphenylmagnesium bromide, which was prepared from, known aryl bromide. Du, C F.; Hart, H.; Na, K. D. J. Org. Chem. 1986, 51, 3165-3169.
    • (1986) J. Org. Chem. , vol.51 , pp. 3165-3169
    • Du, C.F.1    Hart, H.2    Na, K.D.3
  • 48
    • 70350200550 scopus 로고    scopus 로고
    • Another possibility is a boronic acid impurity in the boroxines, which were prepared by heating the corresponding boronic acids at 120 °C under 10 mmHg for 12 h. If the boronic acids remain impure, water is generated by forming boroxine in situ. The use of 4a, dried at 220 °C under 0.5 mmHg for 4 h prior to use, however, did not make a significant difference (6aa, 82%, 98% ee; PhCHO, 6%) under the conditions shown in Table 2, entry 4. Therefore, this possibility was excluded.
    • Another possibility is a boronic acid impurity in the boroxines, which were prepared by heating the corresponding boronic acids at 120 °C under 10 mmHg for 12 h. If the boronic acids remain impure, water is generated by forming boroxine in situ. The use of 4a, dried at 220 °C under 0.5 mmHg for 4 h prior to use, however, did not make a significant difference (6aa, 82%, 98% ee; PhCHO, 6%) under the conditions shown in Table 2, entry 4. Therefore, this possibility was excluded.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.