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Angewandte Chemie International Edition in English
Volumn 30, Issue 1, 1991, Pages 49-69
Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification
Author keywords

Addition; Alcohols; Alkylation; Carbonyl compounds; Catalysis; Chirality transfer; Enantioselectivity; Organometallic compounds; Reaction mechanisms; Synthetic methods
Indexed keywords

EID: 33748247006     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199100491     Document Type: Review
Times cited : (1189)
References (160)
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  • 52
    • 84990077821 scopus 로고    scopus 로고
    • 8]THF, 20°C, THF as internal standard) δ = 1. 27 (t, J = 8. 1 Hz), −0. 71 (q, J = 8. 1 Hz).
  • 56
  • 66
    • 84990083130 scopus 로고    scopus 로고
    • for preparation of enantiomerically pure DAIB, see ref. [13].
  • 100
    • 84990131267 scopus 로고    scopus 로고
    • Reaction of diethylzinc and benzaldehyde in toluene containing 2 mol % (‐)‐DAIB at 50°C for 2 min gave the (S)‐1‐phenyl‐1‐propanol in 94. 6% ee and 70. 2% yield. The blank experiment without (‐)‐DAIB afforded the racemic alcohol in 0. 3% yield, indicating that the S/R ratio in the DAIB catalyzed reaction at 50°C was at most 97. 5:2. 5. The previously recorded value 94. 5:5. 5, obtained by the 1. 5 h reaction [11–13], ignores the participation of the uncatalyzed reaction and hence should be revised.
  • 110
    • 0007436576 scopus 로고
    • (Hexamethylphosphorsäuretriamid)lithiumdicyanmethanid, [LiCH(CH)2(hmpt)]n, eine polymere Verbindung mit dem Malonodinitril-Anion
    • For coordination of pbosphoryl oxygen to two lithium ions see
    • (1988) Chemische Berichte , vol.121 , pp. 1201-1202
    • Jens, K.1    Kopf, J.2    Lorenzen, N.P.3    Weiss, E.4
  • 115
  • 116
    • 84990072184 scopus 로고    scopus 로고
    • Certain γ‐amino alcohols [54] or β‐monoalkylamino alcohols showed opposite selectivities. For example. ethylation of benzaldehyde in the presence of 36, gives (S)‐1‐phenyl‐1‐propanol in 92% ee. In Chaloner's report [51 a], the structure is not really meant to be a Fischer projection and the results quoted there are indeed for (1R, ZS)‐ephedrines and not pseudoephedrine derivatives.
  • 119
    • 37049112125 scopus 로고    scopus 로고
    • 8]toluene at 0 °C gave a singlet at δ = 6. 2 with 10–20% intensity of aldehydic proton signal, which may be assignable to the hemiacetal proton of I. An analogous observation was made in the reaction of n‐butyllithium with benzaldehyde at −85 °C [61], giving compound II with the hemiacetal proton signal at δ = 5. 74. or in the reaction of tetrakis(dialkylamido)titanium with aldehydes at −78 °C (Formula Presented.)
    • J. Chem. Soc. Chem. Commun. , vol.1983 , pp. 406
    • Reetz, M.T.1    Wenderoth, B.2    Peter, R.3
  • 120
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    • A different conclusion was drawn in ref. [50a] and [54].
  • 125
    • 84990121036 scopus 로고    scopus 로고
    • The calculation was made by assuming the product ee to be over 97%.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.